Ethyl 4-oxocyclohexanecarboxylate → Ethyl 4-methylidenecyclohexane-1-carboxylate

HRID 2040898Notes

Reaction equation

HRID 2040898 reaction equation
[CH2:1]=C1CCC2(OCCO2)CC1.O=[C:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.O1C2(CCC(=O)CC2)OCC1>>[CH2:1]=[C:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decane

Product 1

HCID 15151435Ethyl 4-methylidenecyclohexane-1-carboxylateYield 68.7%

Procedure

This intermediate was prepared following the procedure described Compound 31a. As starting material ethyl 4-oxocyclohexane-1-carboxylate replaced 1,4-dioxaspiro[4.5]decan-8-one. After the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 4:6) to give the title compound as a colorless oil. Yield: 68.7%.

Workup

  1. customThis intermediate was prepared
  2. customAfter the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 4:6)

Sources & evidence

ORD record
ord-84a98e0dcd7b4e9685320e61e9f9d044
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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