Sodium Acetate → 2-Benzyloxymethyl-2-benzylthiomethyl-pentanal

HRID 704150Notes

Reaction equation

HRID 704150 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH2:16][S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:13][CH2:14][CH3:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClCCl.C(OCC)C>[CH2:1]([O:8][CH2:9][C:10]([CH2:16][S:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH2:13][CH2:14][CH3:15])[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 20075563HCID 20075563, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 200755792-Benzyloxymethyl-2-benzylthiomethyl-pentanal

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2-Benzyloxymethyl-2-benzylthiomethyl-pentan-1-ol (5 g.) was added to a stirred suspension of pyridinium chlorochromate (5 g.) and anhydrous sodium acetate (3.0 g.) in dry dichloromethane (20 ml.) at 0°, under a current of nitrogen. The mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (100 ml.) and the organic solution was decanted off. The oily residue was treated with ether and the combined extracts were evaporated in vacuo. The residue was chromatographed on silica eluting with ethyl acetate:hexane, 1:10. 2-Benzyloxymethyl-2-benzylthiomethyl-pentanal was obtained as a colourless oil (1.9 g.).

Workup

  1. customthe organic solution was decanted off
  2. additionThe oily residue was treated with ether
  3. customthe combined extracts were evaporated in vacuo
  4. customThe residue was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-1e5841ae552148358c8d39d889574f3a
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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