Potassium bisulfate → 1-Benzofuran-4-carbaldehyde

HRID 1107525Notes

Reaction equation

HRID 1107525 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[O:14][CH:13]=[CH:12][C:11]=12)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1>[O:14]1[C:10]2=[CH:9][CH:8]=[CH:7][C:6]([CH:4]=[O:5])=[C:11]2[CH:12]=[CH:13]1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 18787411HCID 18787411, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 133079811-Benzofuran-4-carbaldehydeYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of N-methoxy-N-methyl-benzofuran-4-carboxamide (3.2 g, 16.6 mmol) in THF (100 mL) was cooled to -45° C. and then LAH (0.7 g, 18.7 mmol) was added. The mixture was stirred for 15 min, allowed to warm to -5° C., and then recooled to -45° C. Saturated KHSO4 (25 mL) was added with vigorous stirring, and the mixture was allowed to warm to room temperature. The precipitate was filtered and washed with acetone. The filtrate was concentrated in vacuo to give an oil (2.3 g, 94%).

Workup

  1. customrecooled to -45° C
  2. temperatureto warm to room temperature
  3. filtrationThe precipitate was filtered
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-65f73360a02c4cca809e0efe03d456cb
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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