(Triphenylphosphoranylidene)acetaldehyde → 3-(2-Triethylsilyl-4-furyl)-2-propen-1-al

HRID 2050651Notes

Reaction equation

HRID 2050651 reaction equation
[CH2:1]([Si:3]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:4]1[O:5][CH:6]=[C:7]([CH:9]=O)[CH:8]=1)[CH3:2].C1(P(=[CH:34][CH:35]=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([Si:3]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:4]1[O:5][CH:6]=[C:7]([CH:9]=[CH:34][CH:35]=[O:36])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-2×

Product 1

HCID 543795853-(2-Triethylsilyl-4-furyl)-2-propen-1-al

Procedure

Reacting 2-triethylsilyl-4-furaldehyde (Compound 5) with (triphenylphosphoranylidene)acetaldehyde gives 3-(2-triethylsilyl-4-furyl)-2-propen-1-al (Compound 45). Conjugate addition of dodecylCu(CN)ZnI (Compound 30) to this aldehyde (Compound 45) gives 4-[1-(2-oxoethyl)tridecyl]-2-triethylsilylfuran (Compound 46). Treatment of this intermediate with manganese dioxide, sodium cyanide and ammonia in tert-butanol, followed by singlet oxygen oxidation gives 4-[1-(2-carboxyamido)methyl]tridecyl-5-hydroxy-2(5H)-furanone (Compound 16).

Sources & evidence

ORD record
ord-49bc4ca2c1cf4e91b06be9b3234fab1f
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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