Piperidine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

HRID 38300

反応式

HRID 38300 の反応式
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=O.N1CCCCC1>C(Cl)(Cl)Cl>[OH:10][C:9]1[CH:8]=[C:7]([CH3:11])[O:6][C:5](=[O:12])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:17][C:16]1[CH:19]=[CH:20][C:21]([O:22][C:23]([F:24])([F:25])[F:26])=[C:14]([Cl:13])[CH:15]=1

参加物

5

反応物 3

HCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

生成物 1

HCID 1363673424-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one収率 10.7%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 1.85 g of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 2.25 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 20 ml of chloroform and 0.7 ml of piperidine was heated under refluxing for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography. Resulting crystals were washed with 40 ml of t-butyl methyl ether to obtain 0.40 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (1a-6]) as a yellow crystal.

後処理

  1. temperaturewas heated
  2. temperatureunder refluxing for 4 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customResulting crystals
  5. washwere washed with 40 ml of t-butyl methyl ether

出典と根拠

ORDレコード
ord-b53064049a3a481eb354075caa462492
出典データセット
uspto-grants-2013_09
特許番号
US08524729B2

関連ノート

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