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

HRID 2215954Notes

Reaction equation

HRID 2215954 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aeab2a383ca34c59975c00ec82c08698
Source dataset
uspto-grants-2006_09
Patent number
US07109357B2

Reaction notes

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