Water → HCID 14752582, compound

HRID 350482Notes

Reaction equation

HRID 350482 reaction equation
[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

Participants

5

Reactant 3

HCID 962WaterHCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)HCID 178418473HCID 178418473, compound

Product 1

HCID 14752582HCID 14752582, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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) δ 1.52–1.60 (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+).

Workup

  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

Sources & evidence

ORD record
ord-03bf08d9928c47139d0e067f19be5f73
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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