Water → 1-Benzofuran-2-Ylmethanol

HRID 1374835Notes

Reaction equation

HRID 1374835 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[C:16](O)=[O:17].O>C(OCC)C.O1CCCC1>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[CH2:16][OH:17]

Participants

6

Reactant 3

HCID 962WaterHCID 10331Benzofuran-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27762631-Benzofuran-2-YlmethanolYield 94.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (467 mg, 12.3 mmol) was suspended in diethyl ether and the suspension was heated under reflux. The suspension was added dropwise with 1-benzofurane-2-carboxylic acid (2.00 g, 12.3 mmol), dissolved in tetrahydrofuran (10 ml) and further heated under reflux for 20 minutes. The reaction mixture was cooled to 0° C., and then added with water (0.8ml) and stirred at the same temperature for 30 minutes. Insoluble solids were removed by filtration using Celite, and then the solvent was evaporated under reduced pressure to obtain the title compound as yellow oil (1.72 g, yield: 94%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux
  3. temperaturefurther heated
  4. temperatureunder reflux for 20 minutes
  5. customInsoluble solids were removed by filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e40f6eb4640e47d7adba8d5b0bde00a1
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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