HCID 10777845, compound → HCID 10753037, compound

HRID 1493070Notes

Reaction equation

HRID 1493070 reaction equation
[CH3:1][N:2]([CH3:19])[C:3](=O)[CH2:4][C:5]1([CH3:17])[CH2:9][C:8]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])=[C:13]([CH3:14])[C:7]=2[O:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:17][C:5]1([CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])[CH2:9][C:8]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])=[C:13]([CH3:14])[C:7]=2[O:6]1

Participants

4

Reactant 2

HCID 10777845HCID 10777845, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10753037HCID 10753037, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-dimethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl acetamide (3.1 g, 11.9 mmol) was dissolved in tetrahydrofuran (50 ml) and lithium aluminum hydride (0.45 g) was added slowly under cooling. The reaction mixture was stirred for 30 minutes at room temperature and then poured into ice-cold water. The product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform-methanol, 95:5) to obtain the desired compound (2.2 g, yield: 81.6%) as oil.

Workup

  1. temperatureunder cooling
  2. additionpoured into ice-cold water
  3. extractionThe product was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (chloroform-methanol, 95:5)

Sources & evidence

ORD record
ord-9402661fb9314331bfc8dc02d9024e72
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Reaction notes

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