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

HRID 489063

Reaction equation

HRID 489063 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-274a806608864003b6ffad9050318002
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Linked notes

Loading…