Dimethyl Sulfide → 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol

HRID 1045404

反応式

HRID 1045404 の反応式
S(C)C.[CH2:4]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1C[O:22]CC1>>[CH2:4]([O:11][CH2:12][CH:13]1[O:14][CH2:15][CH:16]([OH:22])[CH2:17][CH2:18]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

4

実験手順

BH3.SMe2 (17 mL, 1 M in THF) was added slowly to a stirred solution of 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran (2.87 g, 14.06 mmol) (13) in THF (100 mL) at −78° C. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched by the slow addition of 1M NaOH (50 mL) at 0° C. followed by H2O2 (13 mL, 30% in water). The resulting mixture was stirred for 2 hours at room temperature. After aqueous work up the residue was purified on silica gel using EtOAc and hexane to give 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (14).

後処理

  1. customThe mixture was quenched by the slow addition of 1M NaOH (50 mL) at 0° C.
  2. customAfter aqueous work up the residue was purified on silica gel

出典と根拠

ORDレコード
ord-a64bde3197bf4f988a8575630b34b83c
出典データセット
uspto-grants-2013_10
特許番号
US08569283B2

関連ノート

読み込み中…