Triphenylphosphine → 1-(1-Ethynylhexyloxy)-2,3-difluorobenzene

HRID 2244835노트

반응식

HRID 2244835 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH:10]#[C:11][CH:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CC(OC)(C)C>[C:11]([CH:12]([O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])#[CH:10]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 131661-Octyn-3-olHCID 808792,3-DifluorophenolHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 592152391-(1-Ethynylhexyloxy)-2,3-difluorobenzene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 15413tert-Butyl methyl ether용매

실험 절차

42.4 g (0.33 mol) of 2,3-difluorophenol are initially introduced in 1.2 l of THF together with 50.0 ml (0.34 mol) of 1-octyn-3-ol and 94.1 g (0.36 mol) of triphenylphosphine, and a solution of 76.1 ml (0.39 mol) of DIAD in 100 ml of THF is added dropwise. After 19 h at 20° C., the mixture is diluted with MTBE, and the batch is washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane), giving 1-(1-ethynylhexyloxy)-2,3-difluorobenzene as a colourless oil.

후처리

  1. washthe batch is washed with water
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed with sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by column chromatography (SiO2, 1-chlorobutane)

출처 및 근거

ORD 기록
ord-7ca0ce9827224c2c9edb20222dc523d3
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678929B2

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