Sodium borohydride → HCID 69372608, compound

HRID 1827679Notes

Reaction equation

HRID 1827679 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]=[O:11])=[CH:4][N:3]=1.[BH4-].[Na+]>CO.C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][OH:11])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54129332HCID 54129332, compound

Product 1

HCID 69372608HCID 69372608, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-2 (0.5 g, 3.7 mmol) in MeOH (5 mL) and THF (15 mL) at −78° C. was added sodium borohydride (0.042 g, 1.11 mmol) in one portion. After 5 minutes, the cooling bath was removed, and the mixture allowed to warm and stir for 10 minutes. Concentrated HCl (0.3 mL) was added dropwise, and the volume of the mixture reduced to 2 mL by evaporation. Following the addition of sat. NaHCO3 (10 mL), the mixture was extracted with chloroform, the organics dried over MgSO4, and the solvents evaporated to give alcohol 4-3 as a white solid.

Workup

  1. customthe cooling bath was removed
  2. temperatureto warm
  3. additionConcentrated HCl (0.3 mL) was added dropwise
  4. customthe volume of the mixture reduced to 2 mL by evaporation
  5. additionthe addition of sat. NaHCO3 (10 mL)
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialthe organics dried over MgSO4
  8. customthe solvents evaporated

Sources & evidence

ORD record
ord-53c4cddfb6964792b316b425db1602b1
Source dataset
uspto-grants-2006_06
Patent number
US07056909B2

Reaction notes

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