Sodium borohydride → HCID 11224771, compound

HRID 2106447Notes

Reaction equation

HRID 2106447 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[C:19]([CH3:29])[C:20]3[O:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][C:21]=3[CH:28]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[CH:18]=[C:19]([CH3:29])[C:20]2[O:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][C:21]=2[CH:28]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:31])[C:2]([CH3:32])([CH3:33])[CH3:1])=[C:7]([CH3:30])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11316880HCID 11316880, compound

Product 1

HCID 11224771HCID 11224771, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-7-methyl-benzofuran-2-carboxylic acid (250 mg, 0.555 mmol) in THF (10 mL) at RT is treated with NaBH4 (42 mg, 1.11 mmol). The resulting mixture is stirred for 60 min and is quenched with HCl (1.0 N, 5.0 mL) and extracted with EtOAc (2×30 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (170 mg, 68%).

Workup

  1. customis quenched with HCl (1.0 N, 5.0 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb742885cd7d4798a6d8efb61c510f84
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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