Dimethyl Sulfoxide → HCID 14517472, compound

HRID 2249164Notes

Reaction equation

HRID 2249164 reaction equation
Br[C@@H:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])(=[O:16])=[O:15])=[CH:13][C:4]=2[C@H:3]1O.[H-].[Na+].[OH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.CS(C)=[O:37]>>[O:28]=[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]1[C@H:3]1[C@H:2]([OH:37])[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])(=[O:15])=[O:16])=[CH:13][C:4]1=2

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 67946380HCID 67946380, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 14517472HCID 14517472, compound

Conditions

Temperature
60 °C

Procedure

3.5 g (0.0082 mol) of trans-3-bromo-3,4-dihydro-2,2-di-methyl-6-(2-methoxyphenylsulfonyl)-2H benzo[b]pyran-4-ol are added to a suspension of 0.6 g of NaH (80% in oil) (0.0246 mol) and 3.1 g of 2-hydroxypyridine in 50 ml of dimethyl sulfoxide. The mixture is warmed to 60° C. and stirred for 3 hours. The mixture is poured into ice water, and the white precipitate is filtered off with suction and dried in air. Chromatography on silica gel using methanol/ethyl acetate 1:10 gives the product as a white, amorphous powder.

Workup

  1. filtrationthe white precipitate is filtered off with suction
  2. customdried in air
  3. customgives the product as a white, amorphous powder

Sources & evidence

ORD record
ord-4bdf7a4188f84e08ba0ed99aa51251c3
Source dataset
uspto-grants-1991_08
Patent number
US05043344

Reaction notes

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