Sodium borohydride → HCID 22396302, compound

HRID 1070387Notes

Reaction equation

HRID 1070387 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([C:15](O)=[O:16])=[CH:12][C:11]=2[CH:18]=1.[BH4-].[Na+]>C(O)(C)(C)C.CO.[Cl-].[Na+].O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH2:15][OH:16])=[CH:12][C:11]=2[CH:18]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 22396306HCID 22396306, compound

Product 1

HCID 22396302HCID 22396302, compoundYield 61.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-pyridin-2yl-benzofuran-2-carboxylic acid (770 mg, 2.9 mmol) in 28 mL t-butanol and 2.5 mL methanol was added NaBH4 (275 mg, 7.2 mmol). The mixture was heated at 50° C. under argon overnight, allowed to cool, poured into brine, extracted with ethyl acetate, washed with brine, dried (MgSO4), and evaporated. Purification by chromatography gave 404 mg of (5-pyridin-2-yl-benzofuran-2-yl)-methanol. MS: (M+H)+=226.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-a14ed9322603482ebc55b0e3297785ac
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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