Benzyl Bromide → (E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

HRID 1506984ノート

反応式

HRID 1506984 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH2:10][OH:11].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:11][CH2:10]/[CH:9]=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11557356(2E)-3-(2-Chlorophenyl)-2-propen-1-ol

生成物 1

HCID 90033540(E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (E)-3-(2-chlorophenyl) prop-2-en-1-ol(Preparation example 1, 5.3 g, 31.6 mmole) in THF was added NaH (60% in mineral oil, 0.91 g, 37.7 mmole) and Benzyl bromide (4.12 mL, 34.8 mmole), sequently at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.94 g, 70˜90%).

後処理

  1. customsequently at 0° C
  2. customconsumption of SM
  3. customThe reaction mixture was quenched with H2O at 0° C.
  4. extractionthen extracted with EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. customseparated
  7. washThe combined organic layer was washed with H2O
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customThe crude compound was purified by silica ge column

出典と根拠

ORDレコード
ord-d3c51ccb2c9e43839281fb9c2096e137
出典データセット
uspto-grants-2015_12
特許番号
US09221783B2

反応ノート

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