Hydrochloric Acid → HCID 86703748, 화합물

HRID 1849861노트

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HRID 1849861 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86703748HCID 86703748, 화합물수율 54%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1a8ae6534a0b4a0db1873e1fc0e1b6bb
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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