Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate → Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)butyrate

HRID 347417Notes

Reaction equation

HRID 347417 reaction equation
[CH2:1]([C:3](=[CH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([OH:19])[CH2:14]1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH3:2]>CO>[CH2:1]([CH:3]([CH2:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([OH:19])[CH2:14]1)[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 69494094Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate

Product 1

HCID 69494197Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)butyrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.65 g of tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate are dissolved in 50 ml of methanol, and 100 mg of Perlmans catalyst are added. The mixture is stirred under an atmosphere of hydrogen for 24 hours. The catalyst is filtered off through Celite, and the filtrate is then concentrated under reduced pressure. This gives 1.49 g of tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)butyrate as a colorless oil. C16H30O3 (270.40), Rf(n-heptane:ethyl acetate=5:1)=0.10.

Workup

  1. addition100 mg of Perlmans catalyst are added
  2. filtrationThe catalyst is filtered off through Celite
  3. concentrationthe filtrate is then concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d160a2e317b4bd79e0bfc927ce8188c
Source dataset
uspto-grants-2007_02
Patent number
US07173151B2

Reaction notes

Loading…