Hydrochloric Acid → 6-((4-Oxocyclohexyl)oxy)nicotinonitrile

HRID 459914

반응식

HRID 459914 반응식
Cl.CC1(C)CO[C:6]2([CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)[O:5]C1>CC(C)=O>[O:5]=[C:6]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=2)[CH2:10][CH2:9]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 184453076-(3,3-Dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrile

생성물 1

HCID 184453106-((4-Oxocyclohexyl)oxy)nicotinonitrile수율 71%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Combine hydrochloric acid (1.0M aq., 20 mL) with a solution of 6-(3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrile (2000 mg, 6.61 mmol) in acetone (25 mL). Stir at room temperature for 2 h then at 40–50° C. for 1 h. Concentrate the reaction mixture. Partition the residue between EtOAc/hex (25 mL) and K2CO3 (aq. sat. 20 mL). Wash the organic layer with water, brine, and dry it over sodium sulfate, filter and concentrate. Triturate the residue with EtOAc/hexanes (1/4) to provide a white solid which is further purified by flash chromatography (EtOAc/Hexanes 1/4) to give 1010 mg (71% yield) as a white solid.

후처리

  1. waitat 40–50° C. for 1 h
  2. concentrationConcentrate the reaction mixture
  3. customPartition the residue between EtOAc/hex (25 mL) and K2CO3 (aq. sat. 20 mL)
  4. washWash the organic layer with water, brine
  5. dry with materialdry it over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customTriturate the residue with EtOAc/hexanes (1/4)
  9. customto provide a white solid which
  10. customis further purified by flash chromatography (EtOAc/Hexanes 1/4)
  11. customto give 1010 mg (71% yield) as a white solid

출처 및 근거

ORD 기록
ord-a5add9904f4a4db6b932dcaeb14eeb49
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196100B2

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