1-(Triphenylphosphoranylidene)acetone → HCID 67516599, compound

HRID 511747Notes

Reaction equation

HRID 511747 reaction equation
C([O:8][C:9]1[CH:16]2[CH:12]([CH2:13][CH:14]([CH:17]=O)[CH2:15]2)[C:11](=[O:19])[C:10]=1[C:20]1[C:25]([CH2:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:21]=1[CH2:29][CH3:30])C1C=CC=CC=1.[CH:31](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:32]([CH3:34])=[O:33]>ClC(Cl)Cl>[CH2:26]([C:25]1[CH:24]=[C:23]([CH3:28])[CH:22]=[C:21]([CH2:29][CH3:30])[C:20]=1[CH:10]1[C:9](=[O:8])[CH:16]2[CH:12]([CH2:13][CH:14]([CH2:17][CH2:31][C:32](=[O:33])[CH3:34])[CH2:15]2)[C:11]1=[O:19])[CH3:27]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 86702733HCID 86702733, compound

Product 1

HCID 67516599HCID 67516599, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.87 g (4.65 mmol) of 6-(benzyloxy)-5-(2,6-diethyl-4-methylphenyl)-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehyde (compound I-a-2) and 1.63 g (5.11 mmol) of acetonylidenetriphenylphosphorane in 40 ml of trichloromethane are stirred at room temperature for 12 h. The solvent is then removed, and the residue is purified chromatographically on silica gel (mobile phase ethyl acetate/hexane 1:5). This gives 1.37 g (66%) of 3-benzyloxy-2-(2,6-diethyl-4-methylphenyl)-5-(3-oxobut-1-enyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one as a colourless oil.

Workup

  1. customThe solvent is then removed
  2. customthe residue is purified chromatographically on silica gel (mobile phase ethyl acetate/hexane 1:5)

Sources & evidence

ORD record
ord-92da134c1a4f4ba8acae772cbebb8e2c
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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