Hydrochloric Acid → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 4-fluoro-3-anilinobenzyl ether

HRID 1904978노트

반응식

HRID 1904978 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:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][C:21]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C1COCC1>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][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][C:21]=1[NH:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-olHCID 200366814-Fluoro-3-anilinobenzyl bromide

생성물 1

HCID 145808272-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 4-fluoro-3-anilinobenzyl ether

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under a nitrogen atmosphere, 120 mg of sodium hydride (60% oil dispersion) was added to 10 ml of dry THF. A solution of 0.69 of 2-(4-ethoxyphenyl)-3,3,3-trifluoropropanol and 0.82 g or 4-fluoro-3-anilinobenzyl bromide in 20 ml of dry THF was then added with ice-cooling, and the reaction solution was stirred with ice-cooling for 1 hour and at room temperature for 46 hours. Thereafter, the reaction mixture was poured into ice water and adjusted to pH 6 with dilute HCl 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 368 mg 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-2bf2bc0fa39d4f94b3d38d57f68f247b
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04840971

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