Hydrochloric Acid → HCID 86703748、化合物

HRID 1849861ノート

反応式

HRID 1849861 の反応式
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH:3]1[CH2:9][OH:10].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[C:19](F)=[CH:20][C:21]([F:31])=[C:22]([CH:30]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>CS(C)=O>[Cl:17][C:18]1[C:19]([O:10][CH2:9][CH:3]2[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[CH:20][C:21]([F:31])=[C:22]([CH:30]=1)[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 144413(2,6-Dimethylcyclohexyl)methanolHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoate

生成物 1

HCID 86703748HCID 86703748、化合物収率 54%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

To a solution of (2,6-dimethylcyclohexyl)methanol (0.34 g, 2.40 mmol) in anhydrous dimethylsulfoxide (5 mL) were added cesium carbonate (1.56 g, 4.80 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (0.53 g, 2.16 mmol) and the reaction mixture was stirred at 70° C. for 16 hours. The reaction mixture was cooled down and acidified to pH=1 with 5% aqueous hydrochloric acid solution and extracted with ethyl acetate (2×15 mL), the combined organics were washed with brine (15 mL); dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes) afforded the title compound (0.43 g, 54%): MS (ES+) m/z 317.2, 315.2 (M−54); MS (ES−) m/z 315.1, 313.1, (M−56).

後処理

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washthe combined organics were washed with brine (15 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1a8ae6534a0b4a0db1873e1fc0e1b6bb
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

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