Hydrochloric Acid → HCID 86706870, 화합물

HRID 717890

반응식

HRID 717890 반응식
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C([Li])CCC.[O:18]1[CH2:22][CH2:21]OS1(=O)=O.Cl.O.[OH-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:21][CH2:22][OH:18])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 140751,3,2-Dioxathiolane, 2,2-dioxideHCID 14798Sodium HydroxideHCID 108597852-Chloro-4-iodo-6-(trifluoromethyl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 86706870HCID 86706870, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
-78 °C

실험 절차

2-Chloro-4-iodo-6-(trifluoromethyl)pyridine (0.50 g, 1.6 mmol, European Journal of Organic Chemistry, (18), 3793-3798, 2004) was dissolved in tetrahydrofuran (9.0 mL) and cooled to −78° C. 2.5 M n-Butyllithium in hexanes (0.98 mL, 2.4 mmol) was added dropwise. The reaction was stirred at −78° C. for 45 minutes, at which time 1,3,2-dioxathiolane 2,2-dioxide (0.24 g, 2.0 mmol, Aldrich) in Tetrahydrofuran (2.2 mL) was added. The mixture was then allowed to warm to ambient temperature and stir over 1.5 hours. 12.0 M hydrogen chloride in water (0.81 mL, 9.8 mmol) was added to the mixture and the reaction was stirred overnight. 1N NaOH was then added to achieve a pH between 8 and 9, and brine was also added. The product was extracted with EtOAc, and the organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography using a 40 g silica gel cartridge, eluting with a gradient from 0-40% EtOAc in hexanes afforded product as a mixture of isomers, which contained about 50% of the desired isomer (0.09 g, 24%). LCMS (M+H)+: 226.0/228.1.

후처리

  1. additionwas added
  2. temperatureto warm to ambient temperature
  3. stirringthe reaction was stirred overnight
  4. additionwas also added
  5. extractionThe product was extracted with EtOAc
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluting with a gradient from 0-40% EtOAc in hexanes afforded product as a mixture of isomers, which

출처 및 근거

ORD 기록
ord-c46cebcb9f0d4b138e9aa3632173c81c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193733B2

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