Processes of making gamma,delta-unsaturated carboxylic acid and silyl ester thereof, carboxyl group-containing organosilicon compound and process of making

• US 20050070729A1
• Filed: 09/23/2004
• Published: 03/31/2005
• Est. Priority Date: 09/25/2003
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Kiyomori, Ayumu, Kubota, Tohru
• Granted Patent: US 7,307,178 B2
• Time in Patent Office: Days
• US Class Current: 556/443
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/1896 Compounds having one or more Si-O-acyl linkages

Abstract

A γ,δ-unsaturated carboxylic acid silyl ester is prepared by reacting an α,β-unsaturated carboxylic acid ester with a hydrosilane or hydrosiloxane in the presence of tris(pentafluorophenyl)borane. γ,δ-Unsaturated carboxylic acid derivatives are readily prepared through fewer steps and in high yields.

Claims

1. A process of preparing a γ

,δ

-unsaturated carboxylic acid silyl ester of the general formula (3), comprising the step of reacting an α

,β

-unsaturated carboxylic acid ester of the general formula (1) with a hydrosilane or hydrosiloxane of the general formula (2) in the presence of a catalytic amount of tris(pentafluorophenyl)borane,

2. A process of preparing a γ

,δ

-unsaturated carboxylic acid of the general formula (4), comprising the step of desilylating the γ

,δ

-unsaturated carboxylic acid silyl ester of formula (3) resulting from the process of claim 1,

5. A process of preparing an organosilicon compound having a silylated carboxyl group represented by the general formula (5), comprising the step of hydrosilylating the γ

,δ

-unsaturated carboxylic acid silyl ester of formula (3) resulting from the process of claim 1, using a hydrosilane or hydrosiloxane of the general formula (6),

3. An organosilicon compound having a silylated carboxyl group, represented by the general formula (5):

4. The organosilicon compound of claim 3, wherein in formula (5), R¹, R², R⁴, R⁴, R⁵, R⁶, and R^6′

are hydrogen and R³ is methyl.

6. An organosilicon compound having a carboxyl group, represented by the general formula (7):

7. The organosilicon compound of claim 6, wherein in formula (7), R¹, R², R⁴, R^4′

, R⁵, R⁶, and R^6′

are hydrogen and R³ is methyl.

8. A process of preparing an organosilicon compound having a carboxyl group represented by the general formula (7), comprising the step of desilylating an organosilicon compound having a silylated carboxyl group represented by the general formula (5),