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

HRID 1078695
Notes
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Reaction equation

HRID 1078695 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](=[CH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 538759587-[(Trifluoromethylsulfonyl)oxy]-3-phenymethylene-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.

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-657984d3743a4ef6977540748962a198
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05550152

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes