Reaktion #2336523

ord-06a0efca6dbe4ea59034c38495d55a79

Reaktionsgleichung

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
Ausbeute 56.7%

Edukte

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

Reagenzien

CN(C)c1ccncc1
DMAP

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE039991E1uspto-grants-2008_01