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Acetic Acid → (3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde

HRID 1614763
Notes
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Reaction equation

HRID 1614763 reaction equation
[CH2:1]([O:8][C@@H:9]([C@@H:16]([CH:33]=[CH2:34])[CH:17]=[CH:18][C@@H:19](OCC1C=CC=CC=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH:11](OC)OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35](=[O:38])(O)[O-].[Na+].[C:40]([OH:43])(=O)[CH3:41]>O1CCCC1>[CH2:1]([O:8][C@@H:9]([C@@H:16]([CH:33]=[CH2:34])[CH:17]=[CH:18][C@@H:19]([O:43][CH2:40][C:41]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH2:11][CH:35]=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 67862608(3 R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene

Product 1

HCID 86746684(3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

While stirring, 776 mg (1.67 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene [8] described above was heated in a mixture of 13 ml of 80% acetic acid and 2 ml of tetrahydrofuran at 40° C. for 5 hours. Completion of the reaction was confirmed by thin layer chromatography. Then, the reaction solution was poured into saturated sodium bicarbonate aqueous solution. The mixture was extracted 3 times with a solvent mixture of diethyl ether:hexane=7:3. The extracts were combined and washed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 701 mg (1.67 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde [9]. Yield, 100%.

Workup

  1. extractionThe mixture was extracted 3 times
  2. additionwith a solvent mixture of diethyl ether
  3. washwashed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a1f1b823a04c4675aba44ce5e22f6e0c
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05198588

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes