Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoate → 4-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid

HRID 265789Notes

Reaction equation

HRID 265789 reaction equation
CC1(C)C2C=CC(C#CC3C=CC(C(O)=O)=CC=3)=CC=2C(C(C)(C)C)=CC1.[CH3:28][C:29]1([CH3:57])[C:38]2[CH:37]=[CH:36][C:35]([C:39]#[C:40][C:41]3[CH:51]=[CH:50][C:44]([C:45]([O:47]CC)=[O:46])=[CH:43][CH:42]=3)=[CH:34][C:33]=2[C:32]([C:52]#[C:53][CH2:54][CH2:55][CH3:56])=[CH:31][CH2:30]1>>[CH3:28][C:29]1([CH3:57])[C:38]2[CH:37]=[CH:36][C:35]([C:39]#[C:40][C:41]3[CH:42]=[CH:43][C:44]([C:45]([OH:47])=[O:46])=[CH:50][CH:51]=3)=[CH:34][C:33]=2[C:32]([C:52]#[C:53][CH2:54][CH2:55][CH3:56])=[CH:31][CH2:30]1

Participants

3

Reactant 2

HCID 18314569Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoate2×HCID 183145964-[(7,8-Dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoic acid2×

Product 1

HCID 183145594-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl )ethynyl]benzoic acid (Compound 80), 42.0 mg (0.106 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoate (Compound 75) was converted into the title compound (colorless solid) using 11.1 mg (0.27 mmol) of LiOH in H2O in 3 mL of THF/water (3:1, v/v, flushed with argon).

Sources & evidence

ORD record
ord-0019f724c79a4aa38b083ab578ed7f92
Source dataset
uspto-grants-1997_07
Patent number
US05648514

Reaction notes

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