Pentanal → HCID 9997877, compound

HRID 248812Notes

Reaction equation

HRID 248812 reaction equation
[P:1]([O-:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:19](=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)(Cl)Cl>[OH:24][CH:19]([P:1](=[O:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 8063PentanalHCID 21904359Dibenzylphosphite

Product 1

HCID 9997877HCID 9997877, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The general method of F. Texier-Boullet and A. Foucaud [Synthesis, 1982, 916] was employed. A mixture of dibenzyl phosphite (7.73 ml, 0.035 mole) and valeraldehyde (11.15 ml, 0.105 mole) was stirred at room temperature and basic alumina (35 g) added in one portion. After standing overnight at room temperature chloroform was added and the alumina collected and washed with chloroform. The filtrate was evaporated to dryness and the resulting oil chromatographed on silica gel with gradient elution (50% pentane/ethyl acetate-ethyl acetate) to give the title compound as a colourless oil (9.17 g, 76%).

Workup

  1. customFoucaud [Synthesis, 1982, 916]
  2. additionbasic alumina (35 g) added in one portion
  3. customthe alumina collected
  4. washwashed with chloroform
  5. customThe filtrate was evaporated to dryness
  6. customthe resulting oil chromatographed on silica gel with gradient elution (50% pentane/ethyl acetate-ethyl acetate)

Sources & evidence

ORD record
ord-21f63d297ae4462396982f376f1af23d
Source dataset
uspto-grants-1993_05
Patent number
US05212163

Reaction notes

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