Benzoate → Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoate

HRID 277529Notes

Reaction equation

HRID 277529 reaction equation
C([O-])(=O)C1C=CC=CC=1.[CH3:10][C:11]1([CH3:38])[C:20]2[CH:19]=[CH:18][C:17]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)=[CH:16][C:15]=2[C:14]([C:34](C)(C)C)=[CH:13][CH2:12]1.FC(F)(F)S(OC1C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC=2C(C)(C)CC=1)(=O)=O>>[CH3:34][C:14]1[C:15]2[CH:16]=[C:17]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)[CH:18]=[CH:19][C:20]=2[C:11]([CH3:10])([CH3:38])[CH2:12][CH:13]=1

Participants

4

Reactant 3

HCID 242BenzoateHCID 120176384-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester2×HCID 18314564Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate

Product 1

HCID 18314561Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoateYield 0.5%

Procedure

Employing the same general procedure as for the preparation of ethyl 4-(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate (Compound 71), 250 mg (0.52 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66) was converted into the title compound (HPLC Partisil 10, 0.5% EtOAC-hexanes) using 70.2 mg (0.78 mmol) of cuprous cyanide, 33.2 mg (0.78 mmol) of lithium chloride and 34.5 mg (1.28 ml, 1.57 mmol) of methyllithium (1.22M solution in Et2O).

Sources & evidence

ORD record
ord-6379556505b04ff39913b2110ef873eb
Source dataset
uspto-grants-2002_03
Patent number
US06355806B1

Reaction notes

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