Water → HCID 14752582、化合物

HRID 354419ノート

反応式

HRID 354419 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]1[O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([Mg]Cl)[CH:14]=[CH2:15].O>C1COCC1>[CH2:1]([O:8][CH2:9][C@H:10]([OH:12])[CH2:11][CH2:15][CH:14]=[CH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 146296(+)-Benzyl glycidyl etherHCID 178418473HCID 178418473、化合物

生成物 1

HCID 14752582HCID 14752582、化合物収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of benzyl-(S)-glycidyl ether (5.0 g, 30.5 mmol) in THF (100 ml) was added allylmagnesium chloride (1.0 M in Et2O, 30.5 ml, 30.5 mmol) at −78° C., and the resulting mixture was gradually warmed up to rt with stirring. The mixture was poured into water and concentrated in vacuo, then extracted with CHCl3. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give 1-benzyloxy-2-(R)-hydroxy-5-hexene (2.18 g, 35%) as a colorless oil: 1H-NMR (CDCl3) δ1.52-1.60 (m, 2 H), 2.11-2.25 (m, 2 H), 2.34 (d, J=3.2 Hz, 1 H), 3.35 (dd, J=9.6, 8.0 Hz, 1 H), 3.52 (dd, J=9.6, 3.2 Hz, 1 H), 3.84-3.86 (m, 1 H), 4.57 (s, 2 H), 4.96-5.07 (series of m, 2 H), 5.78-5.88 (m, 1 H), 7.29-7.38 (m, 5 H); MS (ESI) m/z, 224 (M++NH4+).

後処理

  1. concentrationconcentrated in vacuo
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent

出典と根拠

ORDレコード
ord-852b6ce47a21496a9defd7befc33538f
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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