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 2393851Notes

Reaction equation

HRID 2393851 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-d0ac46ae5473417c8bf59cb873348ecf
Source dataset
uspto-grants-1998_09
Patent number
US05808083

Reaction notes

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