Water → HCID 13151172, compound

HRID 543471Notes

Reaction equation

HRID 543471 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[CH:11]3[O:13][CH:12]3[C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2].[NH:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23].[H-].[Na+].O>CS(C)=O.C(OCC)(=O)C>[C:1]([C:5]1[CH:17]=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[C@@H:11]([OH:13])[C@H:12]([N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 13222926HCID 13222926, compound

Product 1

HCID 13151172HCID 13151172, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Carbomethoxy-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran (2.42 g, the preparation of which is described in Example 4 of U.K. Pat. No. 1,511,187) and 2-pyrrolidone (0.88 g), were stirred in dimethyl sulphoxide (40 ml) under nitrogen at room temperature. Sodium hydride (0.31 g, 81% dispersion in mineral oil) was added during 5 mins. and the reaction stirred for a further 6 hours. Addition of water, extraction with ethyl acetate, drying or the organic phase with magnesium sulphate, filtration, evaporation and recrystallisation from ethyl acetate-pentane gave 6-carbomethoxy-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]-pyran-3-ol of m.p. 190°-192°.

Workup

  1. customdrying
  2. filtrationthe organic phase with magnesium sulphate, filtration, evaporation and recrystallisation from ethyl acetate-pentane

Sources & evidence

ORD record
ord-ca24158647394ce88990a27f5fd71449
Source dataset
uspto-grants-1984_05
Patent number
US04446113

Reaction notes

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