Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-phenylnaphth-3-yl)ethynyl]benzoate → 4-[(7,8-Dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid

HRID 2393840Notes

Reaction equation

HRID 2393840 reaction equation
CC1(C)C2C=CC([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=CC=2C(C2SC=CN=2)=CC1.[CH3:29][C:30]1([CH3:59])[C:39]2[CH:38]=[CH:37][C:36](C#CC3C=CC(C(OCC)=O)=CC=3)=[CH:35][C:34]=2[C:33]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:32][CH2:31]1>>[CH3:29][C:30]1([CH3:59])[C:39]2[CH:38]=[C:37]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH:36]=[CH:35][C:34]=2[C:33]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:32][CH2:31]1

Participants

3

Reactant 2

HCID 15430594Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-phenylnaphth-3-yl)ethynyl]benzoate2×HCID 223237374-[(7,8-Dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoic acid2×

Product 1

HCID 183145904-[(7,8-Dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoic acid (Compound 78), 27.0 mg (0.07 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-phenylnaphth-3-yl)ethynyl]benzoate (Compound 68) was converted into the title compound (colorless solid) using 5.9 mg (0.14 mmol) of LiOH in H2O.

Sources & evidence

ORD record
ord-96590d85141340f6a85f9f2ed990d785
Source dataset
uspto-grants-1998_09
Patent number
US05808083

Reaction notes

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