Tetrabutylammonium borohydride → HCID 68157561, compound

HRID 242883Notes

Reaction equation

HRID 242883 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 (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 stirred at RT for 1 h. The reaction mixture was quenched by addition of MeOH and volatiles were removed in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) affording the title compound as an oil (452 mg, 98%). LCMS (Method C): RT 3.57 min [M-OH]+ 221.1

Workup

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

Sources & evidence

ORD record
ord-40e5e02974344c31ba241808278df7e9
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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