Tetrabutylammonium borohydride → HCID 68157058, compound

HRID 242890Notes

Reaction equation

HRID 242890 reaction equation
[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([CH3:36])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[S:28][C:29]=1[CH:30]=[O:31]>C1COCC1>[C:19]1([CH3:36])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[S:28][C:29]=1[CH2:30][OH:31]

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 86668874HCID 86668874, compound

Product 1

HCID 68157058HCID 68157058, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium borohydride (800 mg, 3.10 mmol) was added at RT to a solution of 3-o-tolylbenzo[b]thiophene-2-carbaldehyde (2.07 mmol) in THF (10 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 under reduced pressure. The resulting residues was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) affording the title compound as an oil (432 mg, 82% over 2 steps). LCMS (Method C): RT 3.74 min [M-OH]+ 237.1.

Workup

  1. customThe reaction mixture was quenched by addition of MeOH and volatiles
  2. customwere removed under reduced pressure
  3. customThe resulting residues was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-cba0b6f723a942f89638edc13dae137e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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