1-Benzothiophene-2-carbaldehyde → 2-(Hydroxymethyl)benzo[b]thiophene

HRID 1823646Notes

Reaction equation

HRID 1823646 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[BH4-].[Na+]>C1COCC1>[S:1]1[C:5]([CH2:6][OH:7])=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

4

Reactant 2

HCID 7365001-Benzothiophene-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27763352-(Hydroxymethyl)benzo[b]thiopheneYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzo[b]thiophene-2-carbaldehyde (2.216 g, 13.66 mmol) in THF (60 mL) was reacted with sodium borohydride (0.517 g, 13.66 mmol) at room temperature for 3 h. The reaction was quenched with 1N hydrochloric acid at 0° C., the THF evaporated under vacuum and the aqueous residue extracted with diethyl ether. The organic extract was washed with brine, dried over MgSO4 and concentrated to afford the title compound as a yellow solid (2.23 g, 98%).

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid at 0° C.
  2. customthe THF evaporated under vacuum
  3. extractionthe aqueous residue extracted with diethyl ether
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1c875156b52462185587eb0ccc97143
Source dataset
uspto-grants-2006_05
Patent number
US07038077B2

Reaction notes

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