Water → 6-Acetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol

HRID 1905782Notes

Reaction equation

HRID 1905782 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]([CH3:14])([CH3:13])[CH:10]3[O:12][CH:11]3[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[NH:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].[H-].[Na+].O>CS(C)=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]([CH3:14])([CH3:13])[C@@H:10]([OH:12])[C@H:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 13222927HCID 13222927, compound

Product 1

HCID 131511866-Acetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Acetyl-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran (0.33 g, prepared as described in Example 1 of U.K. Pat. No. 1,511,187), and 2-pyrrolidone (0.15 g), were stirred in dimethylsulphoxide (25 ml) under nitrogen at room temperature. Sodium hydride (0.05 g, 80%) was added during 2 mins and the reaction stirred for a further 22 hours. Addition of water, extraction with ethyl acetate, drying of the organic layer with magnesium sulphate, filtration, evaporation and recrystallisation from ethyl acetate gave the title compound (0.04 g) of m.p. 218°-219°.

Workup

  1. dry with materialdrying of the organic layer with magnesium sulphate, filtration, evaporation and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-4741e715544943d3a625079ee0995a70
Source dataset
uspto-grants-1987_03
Patent number
US04647670

Reaction notes

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