4-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester → Ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

HRID 53386Notes

Reaction equation

HRID 53386 reaction equation
[F:1][C:2]([F:33])([F:32])[S:3]([O:6][C:7]1[C:8]2[CH:9]=[C:10](C#CC3C=CC(C(OCC)=O)=CC=3)[CH:11]=[CH:12][C:13]=2[C:14]([CH3:18])([CH3:17])[CH2:15][CH:16]=1)(=[O:5])=[O:4].CC1(C)C2C=C([C:45]#[C:46][C:47]3[CH:57]=[CH:56][C:50]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:49][CH:48]=3)C=CC=2C(=O)CC1>C1COCC1>[F:33][C:2]([F:32])([F:1])[S:3]([O:6][C:7]1[C:8]2[CH:9]=[CH:10][C:11]([C:45]#[C:46][C:47]3[CH:57]=[CH:56][C:50]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:49][CH:48]=3)=[CH:12][C:13]=2[C:14]([CH3:17])([CH3:18])[CH2:15][CH:16]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 120176384-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester2×HCID 15345545Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 18314575Ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66), 800 mg (2.31 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 2 ml of THF was converted into the title compound (white solid) using 466 mg (2.5 ml, 2.54 mmol) of sodium bis(trimethylsilyl)amide (1.0M solution in THF) and a solution of 961 mg (2.54 mmol) of 2-[N,N-bis(trifluoromethylsulfonyloxy)amino]-5-chloropyridine in 2 ml of THF.

Sources & evidence

ORD record
ord-eb4183f4a3ea4546bde86ae79726ae63
Source dataset
uspto-grants-1997_04
Patent number
US05618931

Reaction notes

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