Sodium borohydride → HCID 11213462, compound

HRID 2106430Notes

Reaction equation

HRID 2106430 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([CH3:32])[CH:19]=3)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:33]=1)=[O:4].[BH4-].[Na+]>C1COCC1>[CH3:34][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:16][CH3:17])([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([CH3:32])[CH:19]=3)[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:33]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11213417HCID 11213417, compound

Product 1

HCID 11213462HCID 11213462, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-5-carboxylic acid dimethylamide (45 mg, 0.0972) in THF (5.0 mL) at RT is treated with NaBH4 (7 mg, 0.194 mmol). The resulting mixture is stirred for 1 hour. The reaction is quenched with water (1.0 mL) and extracted with EtOAc (2×20 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (20% EtOAc/Hex) to afford the title compound (45 mg, 99%).

Workup

  1. customThe reaction is quenched with water (1.0 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on column chromatography (20% EtOAc/Hex)

Sources & evidence

ORD record
ord-3e6c0a1dfc4e43159bcf9b4a2e156b69
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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