Réaction #1146853

ord-65b47f23821046a7ab01101309424d24

Équation de réaction

CC1(C)CC(=O)CC(C)(C(=O)O)C1
1,5,5-trimethyl-3-oxo-1-cyclohexylcarboxylic acid
CCC(C)(C)CCO
3,3-dimethylpentanol
CC(C)N=C=NC(C)C
1,3-diisopropylcarbodiimide
→
CC(C)(C)CCOC(=O)C1(C)CC(=O)CC(C)(C)C1
3-(3,3-dimethylbutoxycarbonyl)-3,5,5-trimethylcyclohexanone
Rendement 56.7%

Réactifs

CC1(C)CC(=O)CC(C)(C(=O)O)C1
1,5,5-trimethyl-3-oxo-1-cyclohexylcarboxylic acid
CCC(C)(C)CCO
3,3-dimethylpentanol
CC(C)N=C=NC(C)C
1,3-diisopropylcarbodiimide

Réactifs

CN(C)c1ccncc1
DMAP

Solvants

ClCCl
CH2Cl2

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

1,5,5-trimethyl-3-oxo-1-cyclohexylcarboxylic acid (3.0 g) (M. S. Ziegler and R. M. Herbst, J. Org. Chem. 1951, 16, 920) was treated with 3,3-dimethylpentanol (1.84 g), DMAP (2.21 g) and 1,3-diisopropylcarbodiimide (2.17 g) in CH2Cl2 (80 mL) under standard coupling conditions to give 2.41 g (55% yield) of 3-(3,3-dimethylbutoxycarbonyl)-3,5,5-trimethylcyclohexanone. Mass spectrum (EI) indicated parent ion at m/e 268.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06521622B1uspto-grants-2003_02