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1,3-Propanediol → 3-[5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenoxy]propanol

HRID 1977977
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HRID 1977977 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.CCCCP(CCCC)CCCC.[CH2:36](O)[CH2:37][CH2:38][OH:39].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])(=[O:12])=[O:11])[CH:5]=[C:6]([CH:7]=1)[O:8][CH2:36][CH2:37][CH2:38][OH:39]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 227226495-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol

생성물 1

HCID 227224973-[5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenoxy]propanol수율 95.4%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매

실험 절차

To a solution of 5-methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol (665 mg, 2.0 mmol), as prepared in the preceding step, tri-N-butylphosphine (607 mg, 3.0 mmol), and 1,3-propanediol (760 mg, 10 mmol) in tetrahydrofuran (20 mL) was added 1,1′-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at room temperature overnight. Hexane (30 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (2:1 hexane/ethyl acetate) to give the title compound as a colorless oil (745 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ8.13 (d, J=7.2 Hz, 1H), 7.99 (d, J=7.2 Hz, 1H), 7.80 (t, J=7.6 Hz, 1H), 7.70 (t, J=7.3 Hz, 1H), 6.63 (s, 1H), 6.48 (s, 1H), 6.46 (s, 1H), 4.02 (t, J=6.0 Hz, 2H), 3.81 (m, 2H), 2.25 (s, 3H), 1.99 (m, 2H), 1.61 (s, 1H).

후처리

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (2:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-83bb6604bca64762a605e6676e4c2451
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06235778B1

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