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

HRID 1170653

Reaction equation

HRID 1170653 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-5f272bfbdb2243eb8c4502e1ff98021d
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Linked notes

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