2-Cyclopenten-1-one → HCID 11380123, 화합물

HRID 2417311노트

반응식

HRID 2417311 반응식
Br[C:2]([Br:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[Si](CC)(CC)CC.[C:18]1(=[O:23])[CH2:22][CH2:21][CH:20]=[CH:19]1>[Zn].C(#N)C>[Br:9][C:2]([F:8])([CH:20]1[CH2:21][CH2:22][C:18](=[O:23])[CH2:19]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

6

반응물 3

HCID 135882-Cyclopenten-1-oneHCID 13819ChlorotriethylsilaneHCID 2737168Ethyl 2,2-dibromo-2-fluoroacetate

생성물 1

HCID 11380123HCID 11380123, 화합물

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6342Acetonitrile용매

반응 조건

온도
-20 °C

실험 절차

Under a nitrogen atmosphere, 40.4 g of ethyl dibromofluoroacetate was added dropwise to a suspension of 22.4 mL of chlorotriethylsilane, 8.0 g of zinc, and 250 mL of acetonitrile, over 2 hours at −20° C. The mixture was further stirred for 1.5 hours at −20° C. 2-cyclopenten-1-one in an amount of 5.0 g was added dropwise to the reaction solution, and the mixture was stirred for 15 hours at −20° C. The reaction was quenched with 1M hydrochloric acid, followed by concentration under reduced pressure. After extraction of the residue with diethyl ether twice, the organic layers were combined. The combined organic layer was washed with a saturated aqueous solution of sodium chloride, and was subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=10:1 to 8:1), thereby yielding 6.2 g of (2SR)ethyl 2-bromo-2-fluoro-2-[(1RS)-3-oxocyclopentyl]acetate and 4.4 g of (2RS)ethyl 2-bromo-2-fluoro-2-[(1RS)-3-oxocyclopentyl]acetate.

후처리

  1. stirringthe mixture was stirred for 15 hours at −20° C
  2. customThe reaction was quenched with 1M hydrochloric acid
  3. concentrationfollowed by concentration under reduced pressure
  4. extractionAfter extraction of the residue with diethyl ether twice
  5. washThe combined organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialwas subsequently dried over anhydrous sodium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=10:1 to 8:1)

출처 및 근거

ORD 기록
ord-f2f2ded6b7964af88a9fadf8b7084633
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825375B2

반응 노트

불러오는 중…