Propanal → HCID 10903280, compound

HRID 248811Notes

Reaction equation

HRID 248811 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:22])[CH2:20][CH3:21]>C(Cl)(Cl)Cl>[OH:22][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][CH3:21]

Participants

4

Reactant 2

HCID 527PropanalHCID 21904359Dibenzylphosphite

Product 1

HCID 10903280HCID 10903280, compound

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 (31.13 ml, 0.14 mole) and propionaldehyde (10.21 ml, 1 equiv.) was stirred at room temperature and basic alumina (70 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 clear oil chromatographed on silica gel (600 g) with gradient elution (ether--5% methanol/ether). The title compound was obtained as a clear oil which solidified on standing (27.82 g, 64%). A sample was recrystallized from ether/pentane to give a white crystalline solid, m.p. 81°-82° C.

Workup

  1. customFoucaud [Synthesis, 1982, 916]
  2. additionbasic alumina (70 g) added in one portion
  3. customthe alumina collected
  4. washwashed with chloroform
  5. customThe filtrate was evaporated to dryness
  6. customthe resulting clear oil chromatographed on silica gel (600 g) with gradient elution (ether--5% methanol/ether)

Sources & evidence

ORD record
ord-954dd82f35d849118ada1fe4c9b47660
Source dataset
uspto-grants-1993_05
Patent number
US05212163

Reaction notes

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