Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl ester → HCID 19962316, compound

HRID 53398Notes

Reaction equation

HRID 53398 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.C[C:30]1(C)[C:39]2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=C[C:34]=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][CH2:26][C:27]2[CH:34]=[CH:39][CH:30]=[CH:31][CH:32]=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 19962316HCID 19962316, compound

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-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound (colorless crystals, recrystallized from methyl alcohol) using 268 mg (1.42 mmol) of titanium tetrachloride, 184 mg (1.49 mmol) of benzyl mercaptan and 271 mg (2.82 mmol) of triethylamine.

Sources & evidence

ORD record
ord-c10b49a5209a4e3d940955a7574ef0e3
Source dataset
uspto-grants-1997_04
Patent number
US05618931

Reaction notes

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