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

HRID 2215954ノート

反応式

HRID 2215954 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 112982094-Azido-5-ethoxy-dihydrofuran-2-one収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aeab2a383ca34c59975c00ec82c08698
出典データセット
uspto-grants-2006_09
特許番号
US07109357B2

反応ノート

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