Sodium Acetate → HCID 86757411, compound

HRID 1596713Notes

Reaction equation

HRID 1596713 reaction equation
C([CH2:3]/[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=2[F:26])=[C:13]([O:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:12]=1)=[C:5](/CC)\[C:6]([NH2:8])=[O:7])C.[C:32]([O-])(=O)[CH3:33].[Na+].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=[CH:48][CH:47]=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:47]([N:8]([CH2:32][CH3:33])[C:6](=[O:7])/[CH:5]=[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:20]([F:26])=[CH:21][CH:22]=[CH:23][C:24]=2[F:25])=[C:13]([O:27][CH2:28][CH2:29][CH:30]=[O:31])[CH:12]=1)\[CH3:3])[CH3:48]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2724130Cornforth reagentHCID 86757412HCID 86757412, compound

Product 1

HCID 86757411HCID 86757411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl (E)-3-[4-(2,6-difluorobenzyloxy)-3-(3-hydroxypropoxy)-phenyl]-2-butenamide (2.22 g, 5.13 mmol) and anhydrous sodium acetate (5.05 g, 61.53 mmol) in CH2Cl2 (100 mL) is added pyridinium dichromate (6.63 g, 30.76 mmol) and the mixture is stirred for 2.5 hours. At this time, 2 g celite is added to the mixture, and the resulting mixture is filtered through celite, and the solid is washed with CH2Cl2 (50 mL). The filtrate is concentrated in vacuo, and the residue is filtered through a column of florisil, yielding N,N-diethyl (E)-3-[4-(2,6-difluorobenzyloxy)-3-(3-oxopropyloxy)-phenyl]-2-butenamide, as a brown oil. This crude product is carried on directly to the next step.

Workup

  1. additionAt this time, 2 g celite is added to the mixture
  2. filtrationthe resulting mixture is filtered through celite
  3. washthe solid is washed with CH2Cl2 (50 mL)
  4. concentrationThe filtrate is concentrated in vacuo
  5. filtrationthe residue is filtered through a column of florisil

Sources & evidence

ORD record
ord-0847a67aa6144084a5e72cd937158c1c
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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