Hydrochloric Acid → 3-Benzyloxymethyl-3-benzylthiomethylhexan-2-ol

HRID 704151Notes

Reaction equation

HRID 704151 reaction equation
[CH3:1][Mg]I.[CH2:4]([O:11][CH2:12][C:13]([CH2:19][S:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH2:16][CH2:17][CH3:18])[CH:14]=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(OCC)C>[CH2:4]([O:11][CH2:12][C:13]([CH2:19][S:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH2:16][CH2:17][CH3:18])[CH:14]([OH:15])[CH3:1])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 200755792-Benzyloxymethyl-2-benzylthiomethyl-pentanalHCID 178418373HCID 178418373, compound

Product 1

HCID 200755623-Benzyloxymethyl-3-benzylthiomethylhexan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl magnesium iodide (4.0 ml, 3M solution in ether) was added to a solution of 2-benzyloxymethyl-2-benzylthiomethyl-pentanal (2.6 g.) in dry diethyl ether (50 ml.) at 0°. The mixture was refluxed, with stirring for 2 hours. The mixture was cooled and poured into 1N hydrochloric acid in ice. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on silica, eluting with diethyl ether. 3-Benzyloxymethyl-3-benzylthiomethylhexan-2-ol was obtained as a colourless oil (0.7 g.).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. washThe ethereal extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica
  8. washeluting with diethyl ether

Sources & evidence

ORD record
ord-8c2eed9cae6e45af8702d99b7750eb32
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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