Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl ester → Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-phenylthionaphth-3-yl)ethynyl]benzoate

HRID 53394Notes

Reaction equation

HRID 53394 reaction equation
[CH3:1][C:2]1([CH3:28])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][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:7][C:6]=2[C:5]([S:25][CH2:26][CH3:27])=[CH:4][CH2:3]1.[CH3:29][C:30]1(C)C2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=CC=2C(=O)[CH2:32][CH2:31]1>>[CH3:28][C:2]1([CH3:1])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=3)=[CH:7][C:6]=2[C:5]([S:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:27]=2)=[CH:4][CH2:3]1

Participants

3

Reactant 2

HCID 3025901Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl ester2×HCID 19962326Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-ethylthionaphth-3-yl)ethynyl]benzoate2×

Product 1

HCID 19962320Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-phenylthionaphth-3-yl)ethynyl]benzoate

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-ethylthionaphth-3-yl)ethynyl]benzoate (Compound 151), 500 mg (1.44 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound (colorless flakes, recrystallized from hexane) using 0.268 g (1.42 mmol) of titanium tetrachloride, 172 mg (1.56 mmol) of thiophenol and 291 mg (2.88 mmol) of triethylamine.

Sources & evidence

ORD record
ord-eb216dca3eea43138589885dce137ba0
Source dataset
uspto-grants-1997_04
Patent number
US05618931

Reaction notes

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