Water → 2-(Cyclopropyloxy)-5-(trifluoromethoxy)phenylmethyl Methanesulfonate

HRID 966971ノート

反応式

HRID 966971 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]1([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[CH2:21][OH:22])[CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:22][CH2:21][C:11]1[CH:12]=[C:13]([O:16][C:17]([F:19])([F:20])[F:18])[CH:14]=[CH:15][C:10]=1[O:9][CH:6]1[CH2:7][CH2:8]1)(=[O:4])=[O:3]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222935792-Cyclopropoxy-5-(trifluoromethoxy)benzenemethanol

生成物 1

HCID 222934702-(Cyclopropyloxy)-5-(trifluoromethoxy)phenylmethyl Methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methanesulfonyl chloride (0.31 mL, 0.46 g, 4.0 mmol) was added dropwise to a stirred, cooled (−10° C.) solution of 2-(cyclopropyloxy)-5-(trifluoromethoxy)benzenemethanol (WO9900368, 0.5 g, 2.0 mmol) and triethylamine (0.56 mL, 0.40 g, 4.0 mmol) in dichloromethane (10 mL) and the mixture was stirred at 0° C. for 30 minutes, then at room temperature for 2 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 20 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.28-7.22 (3H, m), 5.20 (2H, s), 3.80-3.77 (1H, m), 3.01 (3H, s), and 0.85-0.79 (4H, m).

後処理

  1. waitat room temperature for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic fractions were washed with aqueous citric acid (10%, 20 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-77e5e1251b8f4eb1ad3e74ff81d869f1
出典データセット
uspto-grants-2005_10
特許番号
US06953792B2

反応ノート

読み込み中…