Tetrabutylammonium borohydride → HCID 68157561, compound

HRID 242854Notes

Reaction equation

HRID 242854 reaction equation
[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][C:26]=2[C:34](=[O:36])[CH3:35])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:19]1([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][C:26]=2[CH:34]([OH:36])[CH3:35])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 13024711HCID 13024711, compound

Product 1

HCID 68157561HCID 68157561, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium borohydride (nBu4NBH4) (750 mg, 2.91 mmol) was added to a solution of 1-(3-phenylbenzofuran-2-yl)ethanone (459 mg, 1.94 mmol) in THF (9 mL) and IMS (1 mL) and the mixture was stirred at RT for 1 h. The reaction mixture was then quenched by addition of MeOH and volatiles were removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) affording 1-(3-phenylbenzofuran-2-yl)ethanol as an oil (452 mg, 98%). LCMS: RT 3.57 min [M−OH]+ 221.1

Workup

  1. customThe reaction mixture was then quenched by addition of MeOH and volatiles
  2. customwere removed under reduced pressure
  3. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-71c851395b0943c8a6242f69632e8bd1
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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