HCID 11716550, 화합물 → 4,4-Difluorobut-3-enylbenzene

HRID 1243979노트

반응식

HRID 1243979 반응식
C1(S([C:10]([F:21])([F:20])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)C=CC=CC=1.CC([O-])(C)C.[K+]>C1COCC1.CN(C=O)C>[F:20][C:10]([F:21])=[CH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

HCID 11716550HCID 11716550, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 53239464,4-Difluorobut-3-enylbenzene수율 85.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Typical Procedures for the Preparation of 1,1-Difluoro-1-alkenes (10) from Alkyl-substitued Difluoromethyl Sulfones (4): Under an argon atmosphere, into a Schlenk flask containing 1,1-difluoro-4-phenylbutyl phenyl sulfone (4g) (100 mg, 0.32 mmol) in THF (4 mL) at −20° C., was added dropwise via a syringe t-BuOK (224 mg, 2 mmol) in DMF (4 mL). The reaction mixture was stirred at −20° C.˜rt for 1 h, and the completion of the reaction was monitored by 19F NMR [δ −89.6 (d, J=46.6 Hz, 1F); −91.6 (dd, J=46.6 Hz, 24.8 Hz, 1F)]. The reaction was then quenched by adding aqueous NaCl solution (10 mL), followed by extraction with Et2O (15 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and the solvent was removed. The crude product was purified by a flash chromatography to give 1,1-difluoro-4-phenyl-1-butene (10a) (46 mg, 85% yield) as a colorless liquid. The characterization data is consistent with that early reported.8h

후처리

  1. customThe reaction was then quenched
  2. additionby adding aqueous NaCl solution (10 mL)
  3. extractionfollowed by extraction with Et2O (15 mL×3)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customThe crude product was purified by a flash chromatography

출처 및 근거

ORD 기록
ord-758ba27d859c499789a9ff5b002b13dc
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119232B2

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