Hydrochloric Acid → HCID 58042516, 화합물

HRID 2048036노트

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HRID 2048036 반응식
[H-].[Na+].[F:3][C:4]1([F:10])[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5]1.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>C1COCC1>[Cl:18][C:17]1[C:12]([O:9][CH2:8][CH:6]2[CH2:7][C:4]([F:10])([F:3])[CH2:5]2)=[N:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 169882,3-DichloropyridineHCID 24758Sodium hydrideHCID 45480377(3,3-Difluorocyclobutyl)methanol

생성물 1

HCID 58042516HCID 58042516, 화합물수율 93.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% dispersion in mineral oil, 1.017 g, 70.6 mmol) was suspended in THF (30.0 mL) and the reaction was cooled to 0° C. under nitrogen with an ice bath. (3,3-Difluorocyclobutyl)methanol (Preparation 2, 2.95 g, 24.2 mmol) in THF (30 mL) was added dropwise to the mixture maintaining the temperature at 0° C. After stirring for 30 minutes, 2,3-dichloropyridine (3.25 g, 22.0 mmol) was added and the suspension was heated to reflux for 16 hours. An aqueous solution of HCl (1.0M, 20 mL) was added and the reaction was extracted with EtOAc (2×100 mL). The combined organics were then dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane,) to afford the title compound (4.82 g, 85%):

후처리

  1. temperaturemaintaining the temperature at 0° C
  2. temperaturethe suspension was heated
  3. temperatureto reflux for 16 hours
  4. extractionthe reaction was extracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organics were then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane,)

출처 및 근거

ORD 기록
ord-d4de9b5ad40049fabe768125b309fc56
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592629B2

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