(Triphenylphosphoranylidene)acetaldehyde → 5-(2-Trimethylsilyl-4-furyl)pent-2-en-1-al

HRID 345893Notes

Reaction equation

HRID 345893 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[O:4][CH:5]=[C:6]([CH2:8][CH2:9][CH:10]=O)[CH:7]=1.C1(P(=[CH:33][CH:34]=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[O:4][CH:5]=[C:6]([CH2:8][CH2:9][CH:10]=[CH:33][CH:34]=[O:35])[CH:7]=1

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 150370923-(2-Trimethylsilyl-4-furyl)propan-1-al

Product 1

HCID 570128945-(2-Trimethylsilyl-4-furyl)pent-2-en-1-al

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Trimethylsilyl-4-furyl)propan-1-al is treated with (triphenylphosphoranylidene) acetaldehyde in tetrahydrofuran to give 5-(2-trimethylsilyl-4-furyl)pent-2-en-1-al which is hydrogenated in the presence of a palladium catalyst to give 5-(2-trimethylsilyl-4-furyl)pentan-1-al. Treating this intermediate with C9H19COCH2PO(OCH3)2 and sodium hydride in tetrahydrofuran gives 3-(7-oxo-5-hexadecenyl)-5-trimethylsilylfuran and oxidizing gives 4-(7-oxo-5-hexadecenyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record
ord-7f4bc989f7cd4be281b3ad9de906ec0b
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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