4-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid → 4-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoic acid

HRID 2256677

Reaction equation

HRID 2256677 reaction equation
[CH3:1][C:2]1([CH3:30])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[CH:5]([O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:4][CH2:3]1.OC1CCC(C)(C)C2C=C(C#CC3C=CC(C(O)=O)=CC=3)C=CC1=2>>[CH3:1][C:2]1([CH3:30])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)[CH:8]=[CH:7][C:6]=2[CH:5]([O:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 183145914-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid2×HCID 19694971Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 196949684-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoate (Compound 111), 83 mg (0.26 mmol) of 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid (Compound 42) was converted into the title compound (white solid) using 0.07 ml (0.65 mmol) of triethylamine and 0.08 ml (0.65 mmol) of chlorotrimethylsilane.

Sources & evidence

ORD record
ord-3a7d3bd229a349579e96af4760d18e9c
Source dataset
uspto-grants-1997_08
Patent number
US05654469

Linked notes

Loading…