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

HRID 1165994ノート

反応式

HRID 1165994 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-d0f9ddf42cfc426fb722a1792ed19065
出典データセット
uspto-grants-1990_03
特許番号
US04912254

反応ノート

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