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

HRID 54795

반응식

HRID 54795 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-346c59c7b65f4ddba6f8c0daab77efe2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623081

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