Monobenzone → 1-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene

HRID 51077ノート

反応式

HRID 51077 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O>CN(C=O)C>[F:30][C:29]([F:32])([F:31])[CH2:28][O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

生成物 1

HCID 227373741-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene収率 106.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a 20 ml DMF solution of 4-benzyloxyphenol (3.35 g, 16.7 mmol) and cesium carbonate (6.02 g, 18.5 mmol) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.29 g, 18.4 mmol) upon cooling in an ice-water bath. The cooling bath was removed and the reaction mixture was heated to 50° C. for 1 hr. The reaction mixture was diluted with AcOEt and water. The organic layer was separated, washed with 1N hydrochloric acid, dried over anhydrous Na2SO4, filtered, and concentrated to give benzyl 4-(2,2,2-trifluoroethoxy)phenyl ether 5.0 g (quant.). This material was dissolved in 200 ml of ethanol and was hydrogenated in a Parr shaker with 10% Pd/C 222 mg under hydrogen atmosphere (50 psi) overnight. The catalyst was removed by suction filtration through a pad of celite. The filtrate was concentrated to give the title compound 2.6 g (87%).

後処理

  1. temperatureupon cooling in an ice-water bath
  2. customThe cooling bath was removed
  3. additionThe reaction mixture was diluted with AcOEt and water
  4. customThe organic layer was separated
  5. washwashed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-deffc2e1647747308a86e634947a8d29
出典データセット
uspto-grants-2004_03
特許番号
US06713508B2

反応ノート

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