Water → (+/-)-4-Bromo-2-(2,4-difluorophenyl)tetrahydrofuran

HRID 54795

反応式

HRID 54795 の反応式
[Br:1][CH:2]([CH2:14]Br)[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])[OH:5].[OH-].[Ca+2].[OH-].[Br-].[Ca+2].[Br-].O>C(OCC)(=O)C.CO>[Br:1][CH:2]1[CH2:14][O:5][CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[F:13])[CH2:3]1

参加物

7

反応物 4

HCID 962WaterHCID 5360316Calcium BromideHCID 6093208Calcium HydroxideHCID 18923963alpha-(2,3-Dibromopropyl)-2,4-difluorobenzenemethanol

生成物 1

HCID 85719042(+/-)-4-Bromo-2-(2,4-difluorophenyl)tetrahydrofuran収率 57%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4.5 g of product from Example 164, 1.67 g of calcium hydroxide, 7.5 g of calcium bromide, 25 ml of water and 12 ml of methyl alcohol is stirred and heated at 85° C. overnight. The reaction mixture is cooled, diluted with ethyl acetate and filtered through diatomaceous earth. The layers are separated and the organic layer is washed with saturated sodium chloride, dried, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel: 3-5% ethyl acetate/hexane) to give 1.96 g of the desired product as a mixture of isomers.

後処理

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through diatomaceous earth
  3. customThe layers are separated
  4. washthe organic layer is washed with saturated sodium chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by chromatography (silica gel: 3-5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-346c59c7b65f4ddba6f8c0daab77efe2
出典データセット
uspto-grants-1997_04
特許番号
US05623081

関連ノート

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