Butyrophenone → 2-(3-Benzyloxy-4-nitrobenzyl)-1-phenylbutan-1-one

HRID 660703

反応式

HRID 660703 の反応式
[C:1]1([C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH2:36]Br)[CH:33]=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH:33]=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39])[CH2:36][CH:8]([CH2:9][CH3:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 10315ButyrophenoneHCID 2733832Lithium HexamethyldisilazideHCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

生成物 1

HCID 688379502-(3-Benzyloxy-4-nitrobenzyl)-1-phenylbutan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 1-phenylbutan-1-one (203 mg, 1.37 mmol) in THF (2.5 mL) at −78° C. is added dropwise LiHMDS (1.62 mL of 1.0 M solution in THF, 1.62 mmol) over a period of 15 min. The solution is stirred at −78° C. for 1 h then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (400 mg, 1.25 mmol) in THF (2.5 mL) is added dropwise. The mixture is allowed to warm to RT and stirred there for 1 h then is quenched with saturated ammonium chloride solution. The mixture is extracted with EtOAc and the organic phase is washed with brine then dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 5-100% EtOAc/hexane as eluent to give the title compound.

後処理

  1. temperatureto warm to RT
  2. stirringstirred there for 1 h
  3. customthen is quenched with saturated ammonium chloride solution
  4. extractionThe mixture is extracted with EtOAc
  5. washthe organic phase is washed with brine
  6. dry with materialthen dried over magnesium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography

出典と根拠

ORDレコード
ord-8d07e62cd094468fb85af82de7512bca
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

関連ノート

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