Pyridine → 1-Ethoxylcarbonyl-cyclopropanyl chloroformate

HRID 1815721

반응식

HRID 1815721 반응식
C1COCC1.[CH2:6]([O:8][C:9]([C:11]1([OH:14])[CH2:13][CH2:12]1)=[O:10])[CH3:7].N1C=CC=CC=1.[C:21](Cl)([Cl:23])=[O:22]>C(Cl)Cl>[Cl:23][C:21]([O:14][C:11]1([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH2:13][CH2:12]1)=[O:22]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylate

생성물 1

HCID 224992811-Ethoxylcarbonyl-cyclopropanyl chloroformate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step 81) A THF solution (50 mL) of 1-hydroxy-cyclopropanecarboxylic acid ethyl ester (5 g, 38.4 mmol) and pyridine (3.3 mL, 41 mmol) was added dropwise a phosgen/toleune solution (25 mL, 47.5 mmol) at 0° C. in 5-10 min. the reaction mixture was allowed slowly warm up overnite. The solid was filtered off and the filtration was concentrated in vacuo. The residue was dissolved in hexane, refiltered, and concentrated in vacuo to afford.7.4 g (100%) the product. The product was dissolved in CH2Cl2 (100 mL) as a stack solution: 1H NMR (300 MHz, CHLOROFORM-D) □ ppm 1.25 (t, J=7.14 Hz, 3H), 1.37 (m, 2H), 1.57 (m, 2H), 4.21 (q, J=6.95 Hz, 2H); (ppm) 13.97, 15.75, 62.07, 62.13, 150.54, 168.71.

후처리

  1. temperaturewas allowed slowly warm up overnite
  2. filtrationThe solid was filtered off
  3. filtrationthe filtration
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in hexane
  6. concentrationconcentrated in vacuo
  7. customto afford

출처 및 근거

ORD 기록
ord-ac99576a227a4a298ffb7013f6502943
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878722B2

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