5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate → 6-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one

HRID 1035606Notes

Reaction equation

HRID 1035606 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.[OH:20][C:21]1[CH:22]=[C:23](OB(O)O)[CH:24]=[CH:25][CH:26]=1>>[OH:20][C:21]1[CH:26]=[C:25]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)[CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonateHCID 217081833-Hydroxyphenylboric acid

Product 1

HCID 114704386-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-oneYield 29%

Procedure

The compound is prepared by the reaction of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl trifluoromethanesulfonate (1.78 g, 6.04 mmol, 1 eq) with 3-hydroxyphenylboric acid (1 g, 7.25 mmol, 1.2 eq) according to method A within 4 h. Purification by column chromatography with dichloromethane as the eluent yields the desired product in a yield of 29%, 900 mg.

Workup

  1. customPurification by column chromatography with dichloromethane as the eluent

Sources & evidence

ORD record
ord-cb734a0c4cd94cde81565e72d9f77466
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

Loading…