Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate → HCID 23361329, compound

HRID 233113Notes

Reaction equation

HRID 233113 reaction equation
CC1(C)C2C=C(C#C[C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)C=CC=2C(=O)CC1.[C:27]([C:29]1[CH:38]=[C:37]2[C:32]([C:33]([CH3:45])([CH3:44])[CH2:34][CH2:35][C:36]2=[C:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:31][CH:30]=1)#[CH:28]>>[CH3:45][C:33]1([CH3:44])[C:32]2[CH:31]=[CH:30][C:29]([C:27]#[C:28][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:38][C:37]=2[C:36](=[C:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 15345545Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate2×HCID 23361324HCID 23361324, compound

Product 1

HCID 23361329HCID 23361329, compound

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1), 235 mg (0.94 mmol) of 7-ethynyl-3,4-dihydro-1(2H)-(3-pentylidene)-4,4-dimethylnaphthalene (Compound X) was converted into the title compound using 236 mg (0.85 mmol) of ethyl 4-iodobenzoate, 57 mg (0.3 mmol) of cuprous iodide and 220 mg (0.31 mmol) of bis(triphenylphosphine)palladium(II) chloride.

Sources & evidence

ORD record
ord-37466c78fab0408d9f6e2e6c985f0d21
Source dataset
uspto-grants-1997_01
Patent number
US05591858

Reaction notes

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