Benzoate → 4-[(5,6-Dihydro-5,5-dimethyl-8-(2-thienyl)-2-naphthalenyl)ethynyl]benzoic acid

HRID 324219Notes

Reaction equation

HRID 324219 reaction equation
CC1(C)CC=C(C2SC=CN=2)C2C=C(C#CC3C=CC(C(O)=O)=CC=3)C=CC1=2.C([O-])(=O)C1C=CC=CC=1.[CH3:38][C:39]1([CH3:67])[CH2:48][CH:47]=[C:46]([C:49]2[S:50][CH:51]=[CH:52][CH:53]=2)[C:45]2[CH:44]=[C:43]([C:54]#[C:55][C:56]3[CH:66]=[CH:65][C:59]([C:60]([O:62]CC)=[O:61])=[CH:58][CH:57]=3)[CH:42]=[CH:41][C:40]1=2>>[CH3:38][C:39]1([CH3:67])[CH2:48][CH:47]=[C:46]([C:49]2[S:50][CH:51]=[CH:52][CH:53]=2)[C:45]2[CH:44]=[C:43]([C:54]#[C:55][C:56]3[CH:57]=[CH:58][C:59]([C:60]([OH:62])=[O:61])=[CH:65][CH:66]=3)[CH:42]=[CH:41][C:40]1=2

Participants

4

Reactant 3

HCID 242BenzoateHCID 10597797Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thienyl)naphth-3-yl)ethynyl]benzoateHCID 223237374-[(7,8-Dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoic acid2×

Product 1

HCID 98430614-[(5,6-Dihydro-5,5-dimethyl-8-(2-thienyl)-2-naphthalenyl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(5,6-dihydro-5,5-dimethyl-8-(2- thiazolyl)-2-naphthalenyl)ethynyl]benzoic acid (Compound 30a), 70.0 mg (0.17 mmol) of ethyl 4-1(5,6- dihydro-5,5-dimethyl-8-(2-thienyl)-2-naphthalenyl)ethynyl]benzoate (Compound 33a) was converted into the title compound (colorless solid) using 17.8 mg (0.42 mmol) of LiOH in H2O. PMR (d6-DMSO): δ 1.27 (6H, s), 2.33 (2H, d, J=4.9 Hz), 6.23 (1H, t, J=4.9 Hz), 7.14 (2H, m), 7.38-7.56 (4H, m), 7.61 (2H, d, J=8.3 Hz), 7.92 (2H, d, J=8.3 Hz).

Sources & evidence

ORD record
ord-00f1ef6b79c54dd880bae31fbf7b1b00
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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