Glyceraldehyde → Benzyl 4,5-dihydroxy-2-pentenoate

HRID 1790815Notes

Reaction equation

HRID 1790815 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH:3]=O.[Br-].[CH2:8]([O:15][C:16]([CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1C(CC)C1>[OH:5][CH:2]([CH2:1][OH:6])[CH:3]=[CH:18][C:16]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17]

Participants

4

Reactant 2

HCID 751GlyceraldehydeHCID 11214019(Benzyloxycarbonylmethyl)triphenylphosphonium bromide

Product 1

HCID 54529065Benzyl 4,5-dihydroxy-2-pentenoate

Reagents, catalysts & solvents 1

HCID 78341,2-EpoxybutaneSolvent

Procedure

A mixture of DL-glycerinaldehyde (4,5 g, 50 mmole) and (benzyloxycarbonylmethyl)-triphenyl-phosphoniumbromide (24.57 g, 50 mmole) in 100 ml 1,2-epoxybutane was refluxed overnight. The mixture was evaporated under vacuum and the product was isolated by silica gel column chromatography.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated under vacuum
  3. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-af17f8c318544e7da024f3bc7e2d6950
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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