Glyceraldehyde → Benzyl 4,5-dihydroxy-2-pentenoate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed overnight
- customThe mixture was evaporated under vacuum
- customthe product was isolated by silica gel column chromatography
Sources & evidence
- ORD record
- ord-5f272bfbdb2243eb8c4502e1ff98021d
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825238B2
Reaction notes
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