Citric Acid → HCID 66747550, compound

HRID 331702Notes

Reaction equation

HRID 331702 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:9]#[N:10])=[CH:4][C:3]=1[O:18][CH3:19].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]#[N:10])=[CH:4][C:3]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 66747569HCID 66747569, compound

Product 1

HCID 66747550HCID 66747550, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (Z)-2-(4-fluoro-3-methoxyphenyl)-3-phenylacrylonitrile (14.23 g, 56.2 mmol) in EtOH was added sodium borohydride (2.66 g, 70.2 mmol) and stirred at room temperature over night. Poured into ice-water, added 5% citric acid and extracted three times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to obtain 15.9 g of an orange oil.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2c7d323ec75f4d149720fff37c6d1aa7
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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