Sodium Hydroxide → HCID 19078579, compound

HRID 234262Notes

Reaction equation

HRID 234262 reaction equation
[OH-].[Na+].C([NH:6][C:7]1[C:8]([CH3:27])=[C:9]([CH3:26])[C:10]2[O:14][C:13]([CH3:23])([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][C:11]=2[C:24]=1[CH3:25])(=O)C>CO.O>[NH2:6][C:7]1[C:8]([CH3:27])=[C:9]([CH3:26])[C:10]2[O:14][C:13]([CH3:23])([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][C:11]=2[C:24]=1[CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19078561HCID 19078561, compound

Product 1

HCID 19078579HCID 19078579, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Aqueous 6N sodium hydroxide solution (3 ml) was added to a solution of 5-acetylamino-2,4,6,7-tetramethyl-2-(2-phenylethyl)-2,3-dihydrobenzofuran (0.7 g, 2.1 mmol) in methanol (3 ml) and the mixture was heated at 200° C. in an autoclave for 18 hours. The reaction mixture was diluted with water and 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 (isopropyl ether-ethyl acetate, 2:1). The crude crystals were recrystallized from hexane to obtain the desired compound (0.32 g, yield: 54.5%), m.p. 45°-46° C. (dec).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 2:1)
  6. customThe crude crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-619d49a8797f4d519b53e0e684565d0f
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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