Methanol → (2S)-2-(Benzyloxy)propanal

HRID 278466Notes

Reaction equation

HRID 278466 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C@@H:19]([CH3:25])[C:20](OCC)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)=O.CC(C)=O.CO>CCCCCC.C(Cl)Cl>[CH2:11]([O:18][C@@H:19]([CH3:25])[CH:20]=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10058881Ethyl (2S)-2-(benzyloxy)propanoateHCID 18522661Acetone cardiceHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11116387(2S)-2-(Benzyloxy)propanalYield 49.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.0M DIBAL (diisobutylaluminum hydride) in hexane (10 ml) was added dropwise to a stirred solution of ethyl (S)-2-(benzyloxy)propionate (obtained in Preparation 7) (2.08 g) in methylene chloride (20 ml) at −78° C. (dry-ice/acetone) for 5 minutes under nitrogen atmosphere. After 20 minutes, methanol (1.6 ml) was added dropwise to the mixture at −78° C., and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was filtered through a pad of Celite, and the solid on the filter was washed with methylene chloride. The combined filtrates were concentrated in vacuo. The obtained residue was purified by silica gel (35 g) chromatography eluted with hexane/ethyl acetate (30:1) to give (S)-2-(benzyloxy)propionaldehyde (810 mg).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe solid on the filter was washed with methylene chloride
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customThe obtained residue was purified by silica gel (35 g) chromatography
  5. washeluted with hexane/ethyl acetate (30:1)

Sources & evidence

ORD record
ord-a299659aa09441b792451ee49187a30d
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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