反応 #53867

反応方程式

trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester

Et3N

dry-ice

DMSO

oxalylchloride

→

(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester

収率 100.4%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   その他to attain RT
2. 2
   その他The mixture was partitioned between Et2O/1N HCl and water
3. 3
   その他The solvent was evaporated under reduced pressure

実験手順

To a dry-ice cooled solution of 8.94 ml (125.9 mmol) DMSO in 150 ml CH2Cl2 was added 5.95 ml (69.24 mmol) oxalylchloride. After 5 min at −78° C., a solution of 16.2 g (66.5 mmol) trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester in 50 ml of CH2Cl2, was added slowly. 10 min later, 43.8 ml (314.75 mmol) of Et3N was added, and the mixture was allowed to attain RT. The mixture was partitioned between Et2O/1N HCl and water. The solvent was evaporated under reduced pressure yielding 16.12 g of clean (4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 241 (m).

出典