Sodium borohydride → HCID 90414955, compound

HRID 578824Notes

Reaction equation

HRID 578824 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:17]O)[C:11]([CH3:16])=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[Cl:19]C1C=C(C2C(OC)=NC(C)=C(C=2)C=O)C=CC=1.[BH4-].[Na+]>CO>[Cl:19][CH2:17][C:10]1[C:11]([CH3:16])=[N:12][C:13]([O:14][CH3:15])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 90414992HCID 90414992, compoundHCID 90417387HCID 90417387, compound

Product 1

HCID 90414955HCID 90414955, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-(3-Chlorophenyl)-6-methoxy-2-methylpyridin-3-yl)methanol. To a solution of 5-(3-chlorophenyl)-6-methoxy-2-methylnicotinaldehyde (350 mg, 1.34 mmol) in methanol (3 mL) was added sodium borohydride (52 mg, 1.3 mmol). The solution was stirred at room temperature for 20 minutes then concentrated under reduced pressure. Purification (FCC, SiO2, 0-50%, EtOAc/hexanes) afforded the title compound (322 mg, 91%). [M+H]=264.06.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customPurification (FCC, SiO2, 0-50%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-624bf81477a44e938a8a350a3c722e27
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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