Dichloromethane → 2-Chloro-1,3-dicyclopropylpropane-1,3-dione

HRID 1455267노트

반응식

HRID 1455267 반응식
Cl[Si](C)(C)C.ClN1[C:11](=O)[CH2:10][CH2:9][C:8]1=[O:13].Cl[CH2:15][Cl:16]>>[Cl:16][CH:15]([C:8]([CH:9]1[CH2:11][CH2:10]1)=[O:13])[C:8]([CH:9]1[CH2:11][CH2:10]1)=[O:13]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 31398Chlorosuccinimide

생성물 1

HCID 219498672-Chloro-1,3-dicyclopropylpropane-1,3-dione

반응 조건

온도
12.5 °C

실험 절차

The diketone described in Preparation 5 (700 g, 4.6 mol) was dissolved in dichloromethane (7 L) with chlorotrimethylsilane (549 g, 5.08 mol), at room temperature. The solution was stirred for 45 minutes, after which time it was cooled to 10 to 15° C. N-chlorosuccinimide (614 g, 4.6 mol) was then added portion-wise, keeping the temperature between 10 and 15° C. The reaction was then warmed to room temperature and stirred for a further 30 minutes. The reaction slurry was then filtered and the organic solution was washed twice with 2M hydrochloric acid (2×1.8 L), followed by two washes with water (2×4.6 L). The organic layer was then dried over anhydrous magnesium sulphate before being concentrated to an oil under vacuum to provide the title compound as a 2:3 mixture of keto:enol tautomers. (780 g, 91%)

후처리

  1. customthe temperature between 10 and 15° C
  2. temperatureThe reaction was then warmed to room temperature
  3. stirringstirred for a further 30 minutes
  4. filtrationThe reaction slurry was then filtered
  5. washthe organic solution was washed twice with 2M hydrochloric acid (2×1.8 L)
  6. dry with materialThe organic layer was then dried over anhydrous magnesium sulphate
  7. concentrationbefore being concentrated to an oil under vacuum

출처 및 근거

ORD 기록
ord-9488a5eae8a14216985c548b19b2bf50
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482375B2

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