252978-96-4 → HCID 18184294, compound

HRID 1358241Notes

Reaction equation

HRID 1358241 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][C:11](O)=[O:12])[C:6]=2[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 9158981252978-96-4HCID 21226445Aluminium lithium hydride

Product 1

HCID 18184294HCID 18184294, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-fluorobenzofuran-3-ylacetic acid (4.6 g, prepared as described in Example 2) in dry tetrahydrofuran (200 mL) was added dropwise to a suspension of lithium aluminium hydride (4.5 g) in dry tetrahydrofuran (150 mL) at room temperature. After reflux for 2 h the reaction was quenched by successive additions of water (9.2 mL), 15% aq. sodium hydroxide (4.6 mL), water (23 mL). Filtration and removal of solvent in vacuo gave an oil, 2-(5-fluorobenzofuran-3-yl)ethanol (4.3 g).

Workup

  1. temperatureAfter reflux for 2 h the reaction
  2. customwas quenched by successive additions of water (9.2 mL), 15% aq. sodium hydroxide (4.6 mL), water (23 mL)
  3. filtrationFiltration and removal of solvent in vacuo

Sources & evidence

ORD record
ord-efdeb311179b47cfb10f9c47503c48f6
Source dataset
uspto-grants-2003_07
Patent number
US06596722B2

Reaction notes

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