Pyrrolidine → 2-dimethoxymethyl-2-methyl-4-oxo-6-phenylsulfonyl-3,4-dihydro-2H-1-benzopyran

HRID 1463278Notes

Reaction equation

HRID 1463278 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C:17](=[O:19])[CH3:18])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]([CH:23]([O:26][CH3:27])[O:24][CH3:25])=O.N1CCCC1>C1(C)C=CC=CC=1>[CH3:25][O:24][CH:23]([O:26][CH3:27])[C:21]1([CH3:20])[CH2:18][C:17](=[O:19])[C:12]2[CH:11]=[C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:15]=[CH:14][C:13]=2[O:16]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 80650Pyruvic aldehyde dimethyl acetalHCID 189877381-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

Product 1

HCID 189877432-dimethoxymethyl-2-methyl-4-oxo-6-phenylsulfonyl-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 100 ml of toluene were dissolved 10 g of the compound obtained in step 4, 6.5 ml of pyruvic aldehyde dimethyl acetal and 1.5 ml of pyrrolidine. The resultant solution was heated to reflux for 16 hours and concentrated reduced pressure to obtain residue, which was purified by silica gel column chormatography using as an eluent a mixture of hexane and ethyl acetate (2:1) to obtain 11 g of the title compound.

Workup

  1. temperatureto reflux for 16 hours
  2. concentrationconcentrated reduced pressure
  3. customto obtain residue, which
  4. customwas purified by silica gel column chormatography
  5. additiona mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-38af4762e5104fb98719c0b01516ec91
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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