Water → 1-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 382835ノート

反応式

HRID 382835 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].Cl[O-].[Na+].O>C(OCC)(=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 99211661-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanolHCID 23665760Sodium Hypochlorite

生成物 1

HCID 102204271-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde収率 84.2%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (20.6 g) was dissolved in ethyl acetate (160 ml) and to the obtained solution were added sodium hydrogencarbonate (2.9 g), tetrabutylammonium bromide (1.6 g) and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinoxy (0.13 g). The mixture was cooled to 5° C. Thereto was added dropwise 12.9% aqueous sodium hypochlorite solution (52.7 g) at 5-10° C. and the mixture was stirred for 1 hr. Water (100 ml) was added to the reaction mixture and the mixture was extracted twice with ethyl acetate (100 ml). The extract was washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine, and silica gel (3 g) was added. The mixture was filtered and the solvent was evaporated to give 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (17.2 g, 84.2%).

後処理

  1. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  2. washThe extract was washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine, and silica gel (3 g)
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-4bb121b3ae5d4551a36d8176b8474c78
出典データセット
uspto-grants-2001_10
特許番号
US06310222B1

反応ノート

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