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

HRID 1873308ノート

反応式

HRID 1873308 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

2.4 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 RT, the batch is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with saturated sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane), giving 1-(1-ethynylhexyloxy)-2,3-difluorobenzene as a colourless oil.

後処理

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

出典と根拠

ORDレコード
ord-99a9c6d81ce54503a22202bff0fb1439
出典データセット
uspto-grants-2012_11
特許番号
US08303844B2

反応ノート

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