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

HRID 751177

반응식

HRID 751177 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8082Piperidine용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f6ab7523c228421a8da74e83dd1e4169
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405236B2

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