Sodium hydride → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-fluorophenoxy)benzyl ether

HRID 1904973노트

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HRID 1904973 반응식
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[CH:8][CH:7]=1)[CH3:4].[F:19][C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[CH2:28]Br)=[CH:22][CH:21]=1>CN(C=O)C>[F:19][C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[CH2:28][O:14][CH2:13][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[CH:11][CH:10]=2)[C:15]([F:16])([F:17])[F:18])=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27374563-(4-Fluorophenoxy)benzyl BromideHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-ol

생성물 1

HCID 145808142-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-fluorophenoxy)benzyl ether수율 77.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Under a nitrogen atmosphere, 171 mg of sodium hydride (60% oil dispersion) was added to 15 ml of dry DMF. A solution of 1.0 g of 2-(4-ethoxyphenyl)-3,3,3-trifluoropropanol and 1.08 g of 3-(4-fluorophenoxy)-benzyl bromide in 20 ml of dry DMF was then added with ice-cooling, and the reaction solution was stirred with ice-cooling for 1 hour and at room temperature for 12 hours. Thereafter, the reaction mixture was poured into dilute HCl-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure, and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (25:1) mixture] to obtain 1.30 g of the desired compound.

후처리

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under a reduced pressure

출처 및 근거

ORD 기록
ord-3db15275476d4c50894ba5f8873e0988
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04840971

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