Hydrochloric Acid → Cyclopentyl[4-(trifluoromethyl)phenyl]methanone

HRID 735890ノート

反応式

HRID 735890 の反応式
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.[CH:17]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18]1.N#N.Cl>C1COCC1>[CH:17]1([C:4]([C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=2)=[O:15])[CH2:21][CH2:20][CH2:19][CH2:18]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamideHCID 178419650HCID 178419650、化合物

生成物 1

HCID 24724174Cyclopentyl[4-(trifluoromethyl)phenyl]methanone収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (0° C.) solution of N-methoxy-N-methyl-4-(trifluoromethyl)benzamide (3.44 g, 14.75 mmol) in anhydrous THF (70 mL) was added dropwise over a period of 30 minutes a solution of cyclopentylmagnesium bromide (2 M in diethyl ether, 29.5 mmol, 14.75 mL) under inert atmosphere of N2. The reaction mixture was slowly allowed to warm to rt overnight. An aqueous solution of HCl (1N, 50 mL) was added and the resulting mixture was extracted with diethyl ether (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over MgSO4, filtered and evaporated under vacuum to give a brown oil (3.0 g). Purification by chromatography (SiO2, DCM/c-Hex 1/3) gave the title compound as a colorless oil (610 mg, 17%). 1H NMR (CDCl3, 300 MHz) δ 8.24 (d, J=8.1 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 3.96-3.79 (m, 1H), 2.21-2.00 (m, 4H), 2.01-1.71 (m, 4H). HPLC (Condition A), Rt: 5.22 min (HPLC purity: 98.6%).

後処理

  1. extractionthe resulting mixture was extracted with diethyl ether (3×50 mL)
  2. washThe combined organic layers were washed with brine (1×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

出典と根拠

ORDレコード
ord-5c4328da20c542e39e7ac026782bbbf3
出典データセット
uspto-grants-2009_09
特許番号
US07592477B2

反応ノート

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