Aluminium lithium hydride → HCID 53798457, compound

HRID 234259Notes

Reaction equation

HRID 234259 reaction equation
[C:1]([NH:4][C:5]1[C:6]([CH3:26])=[C:7]([CH3:25])[C:8]2[O:12][C:11]([CH3:22])([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:10][C:9]=2[C:23]=1[CH3:24])(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:4][C:5]1[C:6]([CH3:26])=[C:7]([CH3:25])[C:8]2[O:12][C:11]([CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)([CH3:22])[CH2:10][C:9]=2[C:23]=1[CH3:24])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23358488HCID 23358488, compound

Product 1

HCID 53798457HCID 53798457, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (20 ml) were added 5-acetylamino-2,4,6,7-tetramethyl-2-[2-(4-fluorophenyl)ethyl]-2,3-dihydrobenzofuran (1.2 g, 3.4 mmol) and lithium aluminum hydride. The mixture was heated under reflux for hours. The reaction mixture was poured into ice water and the product was extracted with ethyl acetate. The extract was washed with water and dried and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 2:1) to obtain the desired compound (0.82 g, yield: 71.2%) as oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for hours
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-993c339edeee48cbb940e5d95e7deb2d
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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