3-Furancarboxaldehyde, 5-(triethylsilyl)- → HCID 54253386, compound

HRID 1032279Notes

Reaction equation

HRID 1032279 reaction equation
[CH2:1]([Si:3]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:4]1[O:8][CH:7]=[C:6]([CH:9]=O)[CH:5]=1)[CH3:2].[O:15]=[C:16]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:17]P(=O)(OCC)OCC.C([Li])CCC>>[CH2:1]([Si:3]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:4]1[O:8][CH:7]=[C:6]([CH:9]=[CH:17][C:16](=[O:15])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-HCID 22165582HCID 22165582, compoundHCID 178418339Butyllithium

Product 1

HCID 54253386HCID 54253386, compound

Procedure

5-Triethylsilyl-3-furaldehyde is reacted with diethyl 2-oxotridecylphosphonate and n-butyl lithium to give 5-triethylsilyl-3-(3-oxo-1-tetradecenyl)furan. Oxidizing using Rose Bengal and oxygen gives 4-(3-oxo-1-tetradecenyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record
ord-c751d9f23695493ab3ba700ebcc65a1a
Source dataset
uspto-grants-1990_09
Patent number
US04957917

Reaction notes

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