Methane → 2-Acetylbutyrolactone
Reaction equation
C.F[C:3]1([C:9](=[O:12])[CH2:10]F)[CH2:8][CH2:7][O:6][C:4]1=[O:5]>>[C:9]([CH:3]1[CH2:8][CH2:7][O:6][C:4]1=[O:5])(=[O:12])[CH3:10]Participants
3
Procedure
The fluorination of 2-Acetyl butyrolactone (3.2 gm, 0.025 m) was carried out in a manner similar to that described in Example 6. Work up gave 2-fluoro-2-acetyl butyrolactone(nc) [NMR (CDCl3); 1H, δH =4.5 ppm (m), 2H; 2.87 ppm (m), 1H; 2.55 ppm (m)1H; 2.47 ppm (d), JHF =5.0 Hz, 3H; 19F, δF =-163.4 ppm (ddqd), J=11.8, 11.8, 4.9, and 1.5 Hz]. Accurate mass measurement:--Found (CI, methane), 147.0442; C6H8O3F requires 147.0457]. A small multiplet at -173.8 ppm and triplet of doublets at -237.9 ppm (Jtriplet =46.3 Hz, Jdoublet =6.8 Hz) in the reaction product were attributed to 2-fluoro-2-(fluoroacetyl)butyrolactone. The conversion was ca. 70% and the yield was ca. 85%.
Sources & evidence
- ORD record
- ord-c84988b0bdf04eb5bb106b2472809939
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06020502
Reaction notes
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