Benzaldehyde → 7-[(Trifluoromethylsulfonyl)oxy]-3-phenylmethyl-benzopyran-4-one

HRID 741724Notes

Reaction equation

HRID 741724 reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:17]=[CH:16][C:10]2[C:11](=[O:15])[CH:12]=[CH:13][O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1CCCC1>CO>[F:19][C:2]([F:1])([F:18])[S:3]([O:6][C:7]1[CH:17]=[CH:16][C:10]2[C:11](=[O:15])[C:12]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 31268PyrrolidineHCID 219555707-Trifluoromethylsulfonyloxy-benzopyran-4-one

Product 1

HCID 153472507-[(Trifluoromethylsulfonyl)oxy]-3-phenylmethyl-benzopyran-4-oneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the product of Step C (27 g, 91.2 mmole) in 183 mL of methanol was added benzaldehyde (11.1 mL, 109 mmole) followed by pyrrolidine (9.1 mL, 109 mmole). The mixture was stirred at room temperature overnight, cooled to 0° C. and filtered. The solid was washed once with 50 mL of ice-cold methanol and then dried in vacuo; 35.2 g, (75% yield) of the title product was recovered. M.P. 133°-135° C.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered
  3. washThe solid was washed once with 50 mL of ice-cold methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-238b63b9c2d94039a2ea751f032824c8
Source dataset
uspto-grants-1996_09
Patent number
US05552435

Reaction notes

Loading…