Citric Acid → HCID 66747923, compound

HRID 591178Notes

Reaction equation

HRID 591178 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]#[N:12].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:11]#[N:12]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 66746789HCID 66746789, compound

Product 1

HCID 66747923HCID 66747923, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(2-fluoro-5-methoxy-phenyl)-3-phenyl-acrylonitrile (5.8 g, 22.90 mmol) in ethanol was added sodium borohydride (1.083 g, 28.6 mmol) and stirred at room temperature over night. The mixture was poured on ice-water and after addition of 5% citric acid extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to obtain an orange oil m=5.68 g (97%).

Workup

  1. additionThe mixture was poured on ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain an orange oil m=5.68 g (97%)

Sources & evidence

ORD record
ord-e57c097ff4d54689958de81d0cfe94dd
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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