Methyl morpholine oxide → 1-[3,5-Bis(trifluoromethyl)phenyl]ethane-1,2-diol

HRID 966966노트

반응식

HRID 966966 반응식
C([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1)=C.C[N+]1([O-])[CH2:23][CH2:22][O:21]CC1.S(=O)(O)[O-:26].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[F:14][C:13]([F:16])([F:15])[C:5]1[CH:4]=[C:3]([CH:22]([OH:21])[CH2:23][OH:26])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

참가 물질

7

반응물 3

HCID 82029Methyl morpholine oxideHCID 27732423,5-Bis(trifluoromethyl)styreneHCID 23665763Sodium Bisulfite

생성물 1

HCID 222935121-[3,5-Bis(trifluoromethyl)phenyl]ethane-1,2-diol수율 98%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 1 mL) was added to a mixture of 1-ethenyl-3,5-bis(trifluoromethyl)benzene (1.85 g, 7.74 mmol) and N-methylmorpholine-N-oxide (1.13 g, 9.67 mmol) in tetrahydrofuran (35 mL) and water (15 mL) and the mixture was stirred at room temperature for 18 hours. Aqueous sodium bisulfite (saturated, 30 mL) was added and the tetrahydrofuran was evaporated under reduced pressure. The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (2.09 g, 98%). 1H NMR (400 MHz, CDCl3) δ 7.86 (2H, s), 7.82 (1H, s), 4.97 (1H, dd, J 8.0, 4.0 Hz), 3.87 (1H, dd, J 11.0, 4.0 Hz), and 3.66 (1H, dd, J 8.0, 11.0 Hz).

후처리

  1. customthe tetrahydrofuran was evaporated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe combined organic fractions were dried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d522b5fd702d4b3e8fa054d430f241fa
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953792B2

반응 노트

불러오는 중…