Sodium borohydride → 1-Hydroxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

HRID 364755Notes

Reaction equation

HRID 364755 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:21])[CH:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH3:15])[CH:7]=[CH:6]2.[BH4-].[Na+]>CO>[CH3:20][S:17]([O:16][CH:14]([CH3:15])[CH:13]([OH:21])[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 132310556-Methoxy-2-naphthyl-2-methylsulfonyloxy-1-propanone

Product 1

HCID 137135381-Hydroxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Representative of Scheme III is the reaction of 1-(6-methoxy-2-naphthyl)-2-methanesulfonyloxypropan-1-one with sodium borohydride in methanol to yield 1-hydroxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate. Treating that material with sodium acetate in acetic acid affords 2-(6-methoxy-2-naphthyl)propanal, which is oxidized with sodium chlorite to 2-(6-methoxy-2-naphthyl)propionic acid. By employing the optically active (S) 1-(6-methoxy-2-naphthyl)-2-methanesulfonyloxypropan-1-one there is obtained, following the same sequential steps, (S) 2-(6-methoxy-2-naphthyl)propionic acid.

Sources & evidence

ORD record
ord-6165992b19604d778243bd7b1461290b
Source dataset
uspto-grants-1986_08
Patent number
US04605758

Reaction notes

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