Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate → Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-2-yl)ethynyl]benzoate

HRID 610333Notes

Reaction equation

HRID 610333 reaction equation
[CH3:1][C:2]1([CH3:29])C2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=CC=2[C:5]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:4][CH2:3]1.FC(F)(F)S(OC1[C:37]2[CH:38]=[CH:39][C:40]([C:48]#[C:49][C:50]3[CH:60]=[CH:59][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:52][CH:51]=3)=[CH:41][C:42]=2C(C)(C)CC=1)(=O)=O>>[CH3:29][C:2]1([CH3:1])[C:38]2[CH:39]=[C:40]([C:48]#[C:49][C:50]3[CH:51]=[CH:52][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:59][CH:60]=3)[CH:41]=[CH:42][C:37]=2[C:5]([C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:4][CH2:3]1

Participants

3

Reactant 2

HCID 18314564Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate2×HCID 18314575Ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 18314563Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-2-yl)ethynyl]benzoate

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), 300 mg (0.63 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 87) was converted into the title compound (colorless oil) using 84 mg (0.94 mmol) of cuprous cyanide, 40 mg (0.94 mmol) of lithium chloride and 120 mg (1.1 ml, 1.88 mmol) of tert-butyllithium (1.7M solution in pentane).

Sources & evidence

ORD record
ord-dc90d861aaa442a29dd4245a00db5ec3
Source dataset
uspto-grants-1999_12
Patent number
US05998471

Reaction notes

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