Pentanal → (E)-tert-Butyl hept-2-enoate

HRID 1617135Notes

Reaction equation

HRID 1617135 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH3:5].[C:7]([O:11][C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])(=[O:13])/[CH:14]=[CH:1]/[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 8063PentanalHCID 256127tert-Butyl (triphenylphosphoranylidene) acetate

Product 1

HCID 15636290(E)-tert-Butyl hept-2-enoateYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of valeraldehyde (5.81 g) in THF (100 mL) was added tert-butoxycarbonylmethylenetriphenylphosphorane (25.4 g) and the reaction mixture stirred for 16 h at rt. The solvents were evaporated, the residue slurried in diethyl ether and filtered. The filtrate was evaporated and the residue purified by chromatography eluting with 3% EtOAc in isohexane to give the subtitle compound 8.5 g.

Workup

  1. customThe solvents were evaporated
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by chromatography
  5. washeluting with 3% EtOAc in isohexane

Sources & evidence

ORD record
ord-6868b74fe59c44079e0e8edabda473da
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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