I2-Ionone → Retinal

HRID 258399

Reaction equation

HRID 258399 reaction equation
O1CCOC1.C(OP([CH2:14][CH:15]=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=[O:20])(OCC)=O)C.CC([O-])(C)C.[K+].[CH3:28][C:29]1[CH2:34][CH2:33][CH2:32][C:31]([CH3:36])([CH3:35])[C:30]=1/[CH:37]=[CH:38]/[C:39]([CH3:41])=O>C1COCC1>[CH3:28][C:29]1[CH2:34][CH2:33][CH2:32][C:31]([CH3:35])([CH3:36])[C:30]=1/[CH:37]=[CH:38]/[C:39](/[CH3:41])=[CH:14]/[CH:15]=[CH:16]/[C:17](/[CH3:21])=[CH:18]/[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 638014I2-IononeHCID 23665647Potassium tert-butoxideHCID 86747400HCID 86747400, compound

Product 1

HCID 638015Retinal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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-d6fb2adbd05e4aa6a024f9565b371433
Source dataset
uspto-grants-1993_11
Patent number
US05266708

Linked notes

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