Tetrabutylammonium borohydride → HCID 68157058, compound

HRID 242862Notes

Reaction equation

HRID 242862 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 (nBu4NBH4) (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 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 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: RT 3.74 min [M-OH]+ 237.1.

Workup

  1. customThe reaction mixture was then 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-6383a86f30a842bfaf1b4c0067a4d71f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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