Bis(2-bromoethyl) ether → Ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate

HRID 2078073노트

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HRID 2078073 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br>CN1C(=O)CCC1.CCOCC>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 3013910Benzeneacetic acid, 4-fluoro-, ethyl ester

생성물 1

HCID 67099334Ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate수율 97%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

A mixture of NaH (1.7 g, 71 mmol) in 100 mL NMP stirred at 0° C., was treated dropwise with a mixture of ethyl 2-(4-fluorophenyl)acetate (5.2 g, 29 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.6 g, 29 mmol) in 20 mL ether. The mixture was allowed to warm to room temperature and stirred for 5 hours, M+1=253. The mixture was then carefully quenched with 100 mL H2O, and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The combined organic layers were then dried over anhydrous Na2SO4 and concentrated in vacuo to give 7.1 g of the crude product as a pale yellow oil. MS (m/z)=253 (M+H)+.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 5 hours
  3. customThe mixture was then carefully quenched with 100 mL H2O
  4. extractionThe mixture was extracted with ether (3×100 mL)
  5. washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
  6. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ed51f6f0241c497f9c22514839cba7b0
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928139B2

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