Sodium hydride → HCID 67099800、化合物

HRID 1868839ノート

反応式

HRID 1868839 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[H-].[Na+].Cl[CH:16](Cl)[CH2:17][O:18][CH2:19][CH:20](Cl)Cl>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:9]([O:11][CH3:12])=[O:10])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 623831,1'-Oxybis(2,2-dichloroethane)HCID 2733230Methyl 2-fluorophenylacetate

生成物 1

HCID 67099800HCID 67099800、化合物収率 52.5%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To an ice-bath cooled, stirred solution of methyl 2-(2-fluorophenyl)acetate (3.4 g, 20 mmol) in THF (100 mL) was added NaH (1.8 g, 44 mmol). The reaction was stirred at 0° C. for 10 minutes and then dichloroethyl ether (2.7 mL, 22 mmol) and tetrabutylammonium bromide (0.33 g, 1.0 mmol) were added sequentially. The yellow reaction mixture was stirred for 16 hours at room temperature and then quenched with a saturated ammonium chloride solution. The aqueous layer was extracted with EtOAc (3×60 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated to afford a yellow oil. Purification by flash chromatography (100% DCM) provided a pale yellow oil (2.5 g). MS m/e=239.0 (M+H)+.

後処理

  1. temperatureTo an ice-bath cooled
  2. stirringThe yellow reaction mixture was stirred for 16 hours at room temperature
  3. customquenched with a saturated ammonium chloride solution
  4. extractionThe aqueous layer was extracted with EtOAc (3×60 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customPurification by flash chromatography (100% DCM)

出典と根拠

ORDレコード
ord-0ce22c459a074c95835504cac870d7b7
出典データセット
uspto-grants-2009_12
特許番号
US07635715B2

反応ノート

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