Diisopropylcarbodiimide → HCID 22175123, compound

HRID 277154Notes

Reaction equation

HRID 277154 reaction equation
[CH3:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH2:3]1.[CH3:14][C:15]([CH3:21])([CH2:19]C)[CH2:16][CH2:17]O.C(N=C=NC(C)C)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][C:15]([CH3:21])([CH3:19])[CH2:16][CH2:17][O:12][C:11]([C:2]1([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][C:4](=[O:10])[CH2:3]1)=[O:13]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 42201903,3-Dimethylpentan-1-olHCID 249751441,3,3-Trimethyl-5-oxocyclohexanecarboxylic acid

Product 1

HCID 22175123HCID 22175123, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Sources & evidence

ORD record
ord-786f67e7741e4659b631272cbdd3d0f9
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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