反应 #1985945

ord-2114d28bad454af9b4c8e60deb539fb3

反应方程式

COC(=O)CCc1cc(OC(C)=O)c(OC)cc1CO[Si](C)(C)C(C)(C)C
methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Cl
HCl
COC(=O)CCc1cc(O)c(OC)cc1CO[Si](C)(C)C(C)(C)C
desired product
COC(=O)CCc1cc(O)c(OC)cc1CO[Si](C)(C)C(C)(C)C
Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取The mixture is extracted with ether
  2. 2
    洗涤the ether solution is washed with brine
  3. 3
    干燥dried over magnesium sulfate
  4. 4
    过滤filtered
  5. 5
    浓缩concentrated in vacuo
  6. 6
    其他The residue is purified by HPLC
  7. 7
    洗涤eluting with 20% ethyl acetate in hexanes

实验过程

A mixture of methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (4.64 g) and potassium carbonate (0.16 g) in anhydrous methanol (50 ml) is stirred at 0°-5° C. for about 18 hours, diluted with water, and the pH adjusted to 5 with dilute HCl. The mixture is extracted with ether and the ether solution is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 20% ethyl acetate in hexanes to give the desired product.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05571506uspto-grants-1996_11