Water → HCID 14743532, compound

HRID 248544Notes

Reaction equation

HRID 248544 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].[O:9]1[CH:15]2[CH:10]1[C:11]([CH3:22])([CH3:21])[O:12][C:13]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=12.O>CS(C)=O.C(OCC)(=O)C>[CH3:21][C:11]1([CH3:22])[C@@H:10]([OH:9])[C@H:15]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])[C:14]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:13]=2[O:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 13222997HCID 13222997, compound

Product 1

HCID 14743532HCID 14743532, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Pyrrolidone (1.02 g) was added to a suspension of sodium hydride (0.3 g, 80% dispersion in oil) in dry dimethyl sulphoxide (20 ml) under nitrogen at room temperature, and the mixture stirred for 1 h. A solution of 3,4-epoxy-3,4-dihydro-2,2,6-trimethyl-2H-1-benzopyran in dry dimethyl sulphoxide (10 ml) was then added, and the reaction mixture stirred for an additional 16 h. Cautious addition of water and extraction via ethyl acetate gave a crude product (1.84 g) which was chromatographed on silica gel and eluted with 60°-80° C. petroleum ether-ethyl acetate mixtures to give a foam (0.7 g) which was recrystallised from 60°-80° C. petroleum ether-ethyl acetate (0.53 g). Two further recrystallisations from ethyl acetatepentane gave the analytical sample of the title compound mp 187°-188° C.

Workup

  1. stirringthe reaction mixture stirred for an additional 16 h
  2. customgave a crude product (1.84 g) which
  3. customwas chromatographed on silica gel
  4. washeluted with 60°-80° C. petroleum ether-ethyl acetate

Sources & evidence

ORD record
ord-4bcef8699dd14764a2ee36c8d674c911
Source dataset
uspto-grants-1993_05
Patent number
US05210234

Reaction notes

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