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

HRID 966966ノート

反応式

HRID 966966 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d522b5fd702d4b3e8fa054d430f241fa
出典データセット
uspto-grants-2005_10
特許番号
US06953792B2

反応ノート

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