CID 406 → Retinal

HRID 893026Notes

Reaction equation

HRID 893026 reaction equation
P(=O)([O-])[O-].[CH3:5][C:6]([O-])(C)[CH3:7].[K+].[CH3:11][C:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[C:13]=1/[CH:20]=[CH:21]/[C:22]([CH3:24])=O.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:11][C:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[C:13]=1/[CH:20]=[CH:21]/[C:22](/[CH3:24])=[CH:7]/[CH:6]=[CH:5]/[C:26](/[CH3:27])=[CH:25]/[CH:29]=[O:28]

Participants

5

Reactant 4

HCID 406CID 406HCID 8028Tetrahydrofuran2×HCID 638014I2-IononeHCID 23665647Potassium tert-butoxide

Product 1

HCID 638015Retinal

Procedure

Phosphonate (I) (0.5 g, 1.72 mmol) in solution in THF (10 ml) was introduced under argon into a 25-ml two-necked flask. Potassium tert-butylate (0.275 g, 2.22 mmol) was added in small portions at -70° C. Stirring was continued at -70° C. for 90 minutes. β-ionone (0.34 g, 1.8 mmol) in solution in THF (1 ml) was then added. The solution was kept at -70° C. for 15 minutes and then at -20° C. for 1 hour.

Workup

  1. waitThe solution was kept at -70° C. for 15 minutes
  2. waitat -20° C. for 1 hour

Sources & evidence

ORD record
ord-873d712e86ef4251897d4620ff9ac346
Source dataset
uspto-grants-1992_06
Patent number
US05120864

Reaction notes

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