4-Pentyn-1-ol → 4-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]-

HRID 751177

反応式

HRID 751177 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH2:13]([OH:18])[CH2:14][CH2:15][C:16]#[CH:17]>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:9]([F:12])([F:11])[O:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]#[C:16][CH2:15][CH2:14][CH2:13][OH:18])=[CH:3][CH:4]=1

参加物

5

反応物 2

HCID 793464-Pentyn-1-olHCID 27772941-Iodo-4-(trifluoromethoxy)benzene

生成物 1

HCID 688226904-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]-収率 83%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8082Piperidine溶媒

反応条件

温度
50 °C

実験手順

A mixture of 1-iodo-4-trifluoromethoxy-benzene (5 g, 17 mmol), Pd(PPh3)4 (973 mg, 1 mmol) and cuprous iodide (160 mg, 1 mmol) in piperidine (130 ml) was stirred for 30 min at 50° C. under an argon atmosphere. 4-Pentyn-1-ol (2.13 g, 25 mmol) was added within 60 min at 50° C. The temperature was raised to 80° C. and the mixture was stirred for 3 h at this temperature. The reaction mixture was cooled to ambient temperature, poured into a solution of saturated aqueous 10% KHSO4/ice water 1/1 and extracted two times with tert butyl methyl ether. The combined extracts were washed with water and brine (two times) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 3.4 g (13.9 mmol, 83%) of the title compound as orange oil.

後処理

  1. temperatureThe temperature was raised to 80° C.
  2. stirringthe mixture was stirred for 3 h at this temperature
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. extractionextracted two times with tert butyl methyl ether
  5. washThe combined extracts were washed with water and brine (two times)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

出典と根拠

ORDレコード
ord-f6ab7523c228421a8da74e83dd1e4169
出典データセット
uspto-grants-2008_07
特許番号
US07405236B2

関連ノート

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