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

HRID 1196422Notes

Reaction equation

HRID 1196422 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(CC1C(=O)C=C(C)CC1)(OCC)=O>C1COCC1>[C:24]([CH2:23][CH:10]1[C:9](=[O:13])[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 825672-Cyclohexen-1-one, 3-phenyl-HCID 2724682Lithium diisopropylamideHCID 216716086-(Carbethoxymethyl)-3-methyl-2-cyclohexen-1-one

Product 1

HCID 216716106-(Carbethoxymethyl)-3-phenyl-2-cyclohexen-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The reaction of 3-phenyl-2-cyclohexen-1-one (3.0 g, 17.4 mmoles) in 10 ml of THF with lithium diisopropylamide (19.2 mmoles) followed by ethyl bromoacetate (3.5 g, 20.9 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. A yield of 3.90 g (87%) of 6-(carbethoxymethyl)-3-phenyl-2-cyclohexen-1-one was obtained.

Sources & evidence

ORD record
ord-ab8f63a2d3cd4cc79025dd91996c8721
Source dataset
uspto-grants-1992_05
Patent number
US05114493

Reaction notes

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