Sodium hydride → HCID 67099800, 화합물

HRID 2078247노트

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HRID 2078247 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 67099800HCID 67099800, 화합물수율 52.5%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b34b7923a43e4d3dbd19b20b2b91d771
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928139B2

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