Acetic Acid → 4-Azido-5-ethoxy-dihydrofuran-2-one

HRID 2215954노트

반응식

HRID 2215954 반응식
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].C(O)(=O)C.[CH2:12]([O:14][CH:15]1[O:19][C:18](=[O:20])[CH:17]=[CH:16]1)[CH3:13].N12CCCN=C1CCCCC2>ClCCl>[N:1]([CH:16]1[CH:15]([O:14][CH2:12][CH3:13])[O:19][C:18](=[O:20])[CH2:17]1)=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 78378AzidotrimethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 32935755-Ethoxy-5H-furan-2-one

생성물 1

HCID 112982094-Azido-5-ethoxy-dihydrofuran-2-one수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

This procedure was carried out in a manner similar to that described by D. J. Guerin, et al., Org. Lett (1999), 1, 1107-1109. To a solution of azidotrimethylsilane (25.8 mL, 0.32 mol) in dichloromethane (400 mL) at room temperature under nitrogen was added acetic acid (18.1 mL, 0.32 mol), and the reaction was stirred for 20 min. 5-Ethoxy-5H-furan-2-one (II, R1=Et) (8.10 g, 0.063 mol) was added dropwise, followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.9 mL, 0.013 mol). The reaction was stirred for 24 h, washed with sodium bicarbonate, dried over sodium sulfate and evaporated. Purification by flash chromatography (SiO2) eluted with 1:9 ethyl acetate:hexanes afforded 4-azido-5-ethoxy-dihydrofuran-2-one (7.85 g, 73% yield) as a colorless oil.

후처리

  1. stirringThe reaction was stirred for 24 h
  2. washwashed with sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customPurification by flash chromatography (SiO2)
  6. washeluted with 1:9 ethyl acetate

출처 및 근거

ORD 기록
ord-aeab2a383ca34c59975c00ec82c08698
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109357B2

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