4-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid → 4-[(5,6-Dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

HRID 2393866Notes

Reaction equation

HRID 2393866 reaction equation
CC1(C)C2C=CC(C#CC3C=CC(C(O)=O)=CC=3)=CC=2C(C#CCCC)=CC1.[CH3:29][C:30]1([CH3:58])[C:39]2[CH:38]=[CH:37][C:36]([C:40]#[C:41][C:42]3[CH:52]=[CH:51][C:45]([C:46]([O:48]CC)=[O:47])=[CH:44][CH:43]=3)=[CH:35][C:34]=2[C:33]([C:53]2[O:54][CH:55]=[CH:56][CH:57]=2)=[CH:32][CH2:31]1>>[CH3:29][C:30]1([CH3:58])[C:39]2[CH:38]=[CH:37][C:36]([C:40]#[C:41][C:42]3[CH:43]=[CH:44][C:45]([C:46]([OH:48])=[O:47])=[CH:51][CH:52]=3)=[CH:35][C:34]=2[C:33]([C:53]2[O:54][CH:55]=[CH:56][CH:57]=2)=[CH:32][CH2:31]1

Participants

3

Reactant 2

HCID 183145594-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid2×HCID 22323712Ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoate2×

Product 1

HCID 158709544-[(5,6-Dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid (Compound 84), 60.3 mg (0.15 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-furyl)naphth-3-yl)ethynyl]benzoate (Compound 122) was converted into the title compound (colorless solid) using 16.0 mg (0.38 mmol) of LiOH in H2O.

Sources & evidence

ORD record
ord-14adb0e976ab4ba494bcdf3b941e7b90
Source dataset
uspto-grants-1998_09
Patent number
US05808083

Reaction notes

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