Reaction equation
C(C1C=CC2OC(C)(C)[C@@H](Br)[C@H](O)C=2C=1)#N.[H-].[Na+].[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[CH:27]3[O:29][CH:28]3[C:23]=2[CH:22]=1)#[N:20].[NH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39]>CS(C)=O.O>[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[C@@H:27]([OH:29])[C@H:28]([N:34]3[CH2:38][CH2:37][CH2:36][C:35]3=[O:39])[C:23]=2[CH:22]=1)#[N:20]Participants
Procedure
A solution of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-bromo-4-hydroxy-2H-benzo[b]pyran (4 g, 14.2 mM) in dimethylsulphoxide (20 ml) was stirred and sodium hydride (60% dispersion in oil, 0.6 g, 15 mM) added. The suspension was stirred for 1 hour when a solution of 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran resulted. 2-Pyrrolidone (1.8 g, 21 mM) and further sodium hydride (0.8 g, 21 mM) were introduced and the mixture stirred at room temperature for an additional 16 hours. Water (40 ml) was slowly added to the mixture to induce crystallisation of the product after which it was cooled in ice and filtered under suction. Crystallisation from ethanol (20 ml) gave the title compound as a cream coloured solid in 60% yield. Recrystallisation from ethyl acetate afforded the pure product as needles, m.p. 226.5°-227.5° having an nmr spectrum and t.l.c. characteristics identical to those of the compound of Example 1.
Workup
- customresulted
- customcrystallisation of the product after which it
- temperaturewas cooled in ice
- filtrationfiltered under suction
- customCrystallisation from ethanol (20 ml)
Sources & evidence
- ORD record
- ord-18990d54dfd54626ab9d8583f24cf826
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04446113
Linked notes
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