Tributylphosphine → Ethyl 3-[2-methyl-4-({[4'-(trifluoromethyl)-3-biphenylyl]methyl}oxy)phenyl]propanoate

HRID 1391733ノート

反応式

HRID 1391733 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=2)=[CH:5][CH:4]=1.P(CCCC)(CCCC)CCCC.O[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:35]([CH3:46])[CH:34]=1>C1COCC1>[CH3:46][C:35]1[CH:34]=[C:33]([O:16][CH2:15][C:11]2[CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:8][CH:7]=3)[CH:14]=[CH:13][CH:12]=2)[CH:38]=[CH:37][C:36]=1[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanolHCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

生成物 1

HCID 69212754Ethyl 3-[2-methyl-4-({[4'-(trifluoromethyl)-3-biphenylyl]methyl}oxy)phenyl]propanoate収率 66.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of [4′-(trifluoromethyl)-3-biphenylyl]methanol (121 mg, 0.48 mmol) in dry THF (5 mL) under nitrogen at 0° C. (ice/water bath) was added nBu3P (240 μL, 0.96 mmol) followed by ethyl 3-(4-hydroxy-2-methylphenyl)propanoate (100 mg, 0.48 mmol) and then ADDM (246 mg, 0.96 mmol) portion-wise. The mixture was stirred at 0° C. for 1 hour, allowed to warm to rt over 21 hours and then partitioned between water and EtOAc, and the layers separated. The aqueous layer was then extracted with EtOAc and the combined organic extract washed with water and then brine, dried (Na2SO4) and the solvent removed under vacuum. Purification by flash chromatography (silica) eluting with cyclohexane:EtOAc (15:1) afforded the title compound as a clear oil (141 mg).

後処理

  1. temperatureto warm to rt over 21 hours
  2. custompartitioned between water and EtOAc
  3. customthe layers separated
  4. extractionThe aqueous layer was then extracted with EtOAc
  5. extractionthe combined organic extract
  6. washwashed with water
  7. dry with materialbrine, dried (Na2SO4)
  8. customthe solvent removed under vacuum
  9. customPurification by flash chromatography (silica)
  10. washeluting with cyclohexane:EtOAc (15:1)

出典と根拠

ORDレコード
ord-02fba1fd6e1a4ad79cea87c165b9f885
出典データセット
uspto-grants-2008_03
特許番号
US07338960B2

反応ノート

読み込み中…