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

HRID 1904978ノート

反応式

HRID 1904978 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2bf2bc0fa39d4f94b3d38d57f68f247b
出典データセット
uspto-grants-1989_06
特許番号
US04840971

反応ノート

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