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

HRID 277548Notes

Reaction equation

HRID 277548 reaction equation
CC1(C)C2C=C(C#CC3C=CC(C(O)=O)=CC=3)C=CC=2C(C2C=CC=CC=2)=CC1.[CH3:30][C:31]1([CH3:59])[C:40]2[CH:39]=[C:38]([C:41]#[C:42][C:43]3[CH:53]=[CH:52][C:46]([C:47]([O:49]CC)=[O:48])=[CH:45][CH:44]=3)[CH:37]=[CH:36][C:35]=2[C:34]([C:54]2[S:55][CH:56]=[CH:57][N:58]=2)=[CH:33][CH2:32]1>>[CH3:30][C:31]1([CH3:59])[C:40]2[CH:39]=[C:38]([C:41]#[C:42][C:43]3[CH:53]=[CH:52][C:46]([C:47]([OH:49])=[O:48])=[CH:45][CH:44]=3)[CH:37]=[CH:36][C:35]=2[C:34]([C:54]2[S:55][CH:56]=[CH:57][N:58]=2)=[CH:33][CH2:32]1

Participants

3

Reactant 2

HCID 18314579Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-2-yl)ethynyl]benzoate2×HCID 183145904-[(7,8-Dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid2×

Product 1

HCID 183145584-[(7,8-Dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-2-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid (Compound 97), 177 mg (0.43 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-2-yl)ethynyl]benzoate (Compound 88) was converted to the title compound (white solid) using 91 mg (4.3 ml, 2.14 mmol) of LiOH (0.5M aqueous solution).

Sources & evidence

ORD record
ord-b643f9bcea7d40b490cd8f414773b5cd
Source dataset
uspto-grants-2002_03
Patent number
US06355806B1

Reaction notes

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