Sodium borohydride → HCID 67373307, compound

HRID 717750Notes

Reaction equation

HRID 717750 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6](/[CH:8]=[C:9](/[C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)\[C:10]#[N:11])[CH:7]=1.[BH4-].[Na+]>C1COCC1.CO.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH2:8][CH:9]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67373302HCID 67373302, compound

Product 1

HCID 67373307HCID 67373307, compoundYield 91.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of (Z)-3-(5-methyl-2-nitrophenyl)-2-(6-methylpyridin-3-yl)acrylonitrile (6.5 g, 0.0232 mol) in THF (44 mL) and MeOH (135 mL) was added sodium borohydride (1.7 g, 0.0465 mol) at 0° C. under nitrogen atmosphere. After the addition, the reaction mixture was stirred for 2 h at 0° C. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water (100 mL), and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, and solvent was removed under reduced pressure to obtain product as a yellow colored solid (6 g, 91.7% yield).

Workup

  1. additionAfter the addition
  2. customAfter completion of reaction (monitored by TLC)
  3. extractionextracted with EtOAc (3×150 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate, and solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-be7e7e6cd170492db35b887c825d0144
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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