Ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate → Ethyl 6-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-naphth-3-yl)ethynyl]nicotinate

HRID 1233

Reaction equation

HRID 1233 reaction equation
OC1CCC(C)(C)C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC1=2.[CH3:27][C:28]1([CH3:52])[C:37]2[CH:36]=[CH:35][C:34]([C:38]#[C:39][C:40]3[CH:50]=[CH:49][C:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:42][N:41]=3)=[CH:33][C:32]=2[C:31](=[O:51])[CH2:30][CH2:29]1>>[OH:51][CH:31]1[CH2:30][CH2:29][C:28]([CH3:52])([CH3:27])[C:37]2[CH:36]=[CH:35][C:34]([C:38]#[C:39][C:40]3[CH:50]=[CH:49][C:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:42][N:41]=3)=[CH:33][C:32]1=2

Participants

3

Reactant 2

HCID 15391668Ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate2×HCID 15391671Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 18314597Ethyl 6-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-naphth-3-yl)ethynyl]nicotinate

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9), 700 mg (2 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 4) was converted into the title compound using 60 mg (1.6 mmol) of sodium borohydride.

Sources & evidence

ORD record
ord-a309b213ee744acf9636717f3498282d
Source dataset
uspto-grants-1998_03
Patent number
US05723620

Linked notes

Loading…