Ethyl bromoacetate → 6-(Carbethoxymethyl)-3-n-butyl-2-cyclohexen-1-one

HRID 1196421Notes

Reaction equation

HRID 1196421 reaction equation
[CH2:1]([C:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH:6]=1)[CH2:2][CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(CC1C(=O)C=C(C)CC1)(OCC)=O>C1COCC1>[C:22]([CH2:21][CH:8]1[C:7](=[O:11])[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:9]1)([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 2390953-Butylcyclohex-2-en-1-oneHCID 2724682Lithium diisopropylamideHCID 216716086-(Carbethoxymethyl)-3-methyl-2-cyclohexen-1-one

Product 1

HCID 216716096-(Carbethoxymethyl)-3-n-butyl-2-cyclohexen-1-oneYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The reaction of 3-n-butyl-2-cyclohexen-1-one (3.0 g, 19.7 mmoles) in 10 ml of THF with lithium diisopropylamide (2.17 mmoles) followed by ethyl bromoacetate (3.96 g, 23.6 mmoles) in 10 ml of THF, at -78° C. under argon, was conducted in a similar manner to the synthesis of 6-(carbethoxymethyl)-3-methyl-2-cyclohexen-1-one described in Example II, and a yield of 3.92 g (83%) of 6-(carbethoxymethyl)-3-n-butyl-2-cyclohexen-1-one was obtained.

Sources & evidence

ORD record
ord-b392d21db49140da94f5a98682872e59
Source dataset
uspto-grants-1992_05
Patent number
US05114493

Reaction notes

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