HCID 11716550、化合物 → 4,4-Difluorobut-3-enylbenzene

HRID 1243979ノート

反応式

HRID 1243979 の反応式
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

参加物

5

反応物 2

HCID 11716550HCID 11716550、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 53239464,4-Difluorobut-3-enylbenzene収率 85.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-758ba27d859c499789a9ff5b002b13dc
出典データセット
uspto-grants-2006_10
特許番号
US07119232B2

反応ノート

読み込み中…