Acetic Anhydride → 1-[4-(Morpholine-4-sulfonyl)-3-trifluoromethyl-phenyl]-ethanone

HRID 1098748ノート

反応式

HRID 1098748 の反応式
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[C:9]([C:22]([F:25])([F:24])[F:23])[CH:8]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C.O>[N:16]1([S:13]([C:10]2[CH:11]=[CH:12][C:7]([C:26](=[O:28])[CH3:27])=[CH:8][C:9]=2[C:22]([F:25])([F:24])[F:23])(=[O:15])=[O:14])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

参加物

8

反応物 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 473151804-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-morpholineHCID 178418918HCID 178418918、化合物

生成物 1

HCID 595062911-[4-(Morpholine-4-sulfonyl)-3-trifluoromethyl-phenyl]-ethanone収率 44.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of isopropylmagnesium chloride (2M in THF, 10 ml, 20.04 mmol) was added drop wise to a solution of the product obtained in step 1 (5.00 g, 13.36 mmol) in THF (30 ml) at −10° C. The mixture was stirred at this temperature for 1 h and then added drop wise to acetic acid anhydride (12.6 ml, 133.60 mmol) at −15° C. The reaction mixture was stirred at 0° C. for 2 h and allowed to warm up slowly to RT. Water (100 ml) was added and the reaction mixture was stirred at 60° C. for 15 min. The mixture was diluted with ethyl acetate at RT, neutralized with aqueous NaHCO3, washed with brine, dried over sodium sulphate and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (2.00 g, 44%).

後処理

  1. stirringThe reaction mixture was stirred at 0° C. for 2 h
  2. stirringthe reaction mixture was stirred at 60° C. for 15 min
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customPurification of the crude product by silica gel chromatography

出典と根拠

ORDレコード
ord-27884c8f32cb4432aceb1087f90ab2a6
出典データセット
uspto-grants-2012_03
特許番号
US08143242B2

反応ノート

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