反应 #742260

反应方程式

(E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid

1-tert-butyl-4-(3-ethoxy-2-methyl-allyl)-benzene

3-(4-tert-butyl-phenyl)-2-methyl-propionaldehyde

→

ester

收率 28.2%

(E)-3(2-Hydroxy-phenyl)-acrylic acid 3(4-tert-butyl-phenyl)-1-ethoxy-propyl ester

收率 28.2%

溶剂

THF

toluene

反应条件

后处理

1. 1
   其他The reaction mixture was partitioned between saturated sodium carbonate and hexane
2. 2
   洗涤the organic layer was washed with brine
3. 3
   干燥dried over (Na2SO4)
4. 4
   其他evaporated to dryness
5. 5
   其他to yield 5.3 g of the crude intermediate (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid 3-(4-tert-butyl-phenyl)-1-ethoxy-propyl ester as a pale yellow oil
6. 6
   浓缩the mixture was concentrated
7. 7
   其他purification by repeated flash chromatography

实验过程

A solution of 3.1 g of (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid, 3.0 g of 1-tert-butyl-4-(3-ethoxy-2-methyl-allyl)-benzene, accessible from 3-(4-tert-butyl-phenyl)-2-methyl-propionaldehyde via a two step procedure according to P. D. Bartlett and A A. Frimer, Heterocycles 11, 419-435, (1978), and 20 mg of p-TSA in 25 ml of toluene was stirred at 0° C. for 4 h and at room temperature for 14 h. The reaction mixture was partitioned between saturated sodium carbonate and hexane and the organic layer was washed with brine, dried over (Na2SO4) and evaporated to dryness to yield 5.3 g of the crude intermediate (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid 3-(4-tert-butyl-phenyl)-1-ethoxy-propyl ester as a pale yellow oil. This was dissolved in 20 ml of THF and treated at 0° C. with 3.2 g of solid TBAF-3H2O. After 30 min., the mixture was concentrated and purification by repeated flash chromatography yielded 1.2 g of the title ester (a mixture of diastereoisomers) as a pale yellow oil.

来源