Water → HCID 14752582, 화합물

HRID 354419노트

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HRID 354419 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 146296(+)-Benzyl glycidyl etherHCID 178418473HCID 178418473, 화합물

생성물 1

HCID 14752582HCID 14752582, 화합물수율 35%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-852b6ce47a21496a9defd7befc33538f
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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