Sodium borohydride → HCID 178472331, compound

HRID 2368132Notes

Reaction equation

HRID 2368132 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]3[CH:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][C:21](=[O:23])[CH3:22])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]3[CH:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][CH:21]([OH:23])[CH3:22])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178472330HCID 178472330, compound

Product 1

HCID 178472331HCID 178472331, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-({trans-4-[6-(cyclopropylmethoxy)-1-benzofuran-2-yl]cyclohexyl}oxy)propan-2-one (556 mg) in ethanol (10 mL) was added sodium borohydride (123 mg) under ice-cooling. The mixture was stirred at 0° C. for 1 hr and extracted with ethyl acetate and 1M hydrochloric acid. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (555 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate and 1M hydrochloric acid
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bacd389f5f9f421a84b7e46d0dfb5b8b
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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