3',5'-Difluoroacetophenone → 2-(3,5-Difluorophenyl)propan-2-ol

HRID 705186

반응식

HRID 705186 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:12][Mg]Br>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])([CH3:12])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 5185963',5'-DifluoroacetophenoneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 577321592-(3,5-Difluorophenyl)propan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(3,5-difluorophenyl)ethanone (1.0 equiv) in THF (0.2 M) at 0° C. was added methylmagnesium bromide (1.0 M in THF, 1.15 equiv). After stirring for 4 hours the reaction was quenched by addition of NH4Cl(sat), diluted with EtOAc, washed with NaCl(sat), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography to yield 2-(3,5-difluorophenyl)propan-2-ol. To a solution of 2-(3,5-difluorophenyl)propan-2-ol in CH2Cl2 (0.1 M) at 0° C. was added 2,6 lutidine (6 equiv.) and than triisopropylsilyl trifluoromethanesulfonate (3.0 equiv.). After stirring for 3 hours at 0° C. and six hours at rt the solution was partitioned between EtOAc and NaHCO3(sat), separated, washed with NaCl(sat), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography to yield (2-(3,5-difluorophenyl)propan-2-yloxy)triisopropylsilane. (400 MHz, <cdcl3>) δ ppm 1.05-1.08 (m, 21 H) 1.57 (s, 6 H) 6.63 (s, 1 H) 7.00 (dd, J=9.39, 2.35 Hz, 2 H).

후처리

  1. customwas quenched by addition of NH4Cl(sat)
  2. additiondiluted with EtOAc
  3. washwashed with NaCl(sat)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by ISCO SiO2 chromatography

출처 및 근거

ORD 기록
ord-044e148c4ab54996ba08bcc06ca37a6f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173883B2

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