(Diethylamino)sulfur trifluoride → [(4R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl fluoride

HRID 561232Notes

Reaction equation

HRID 561232 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8](O)=[O:9])[C:4](=[O:11])[O:3]1.C(N(S(F)(F)[F:19])CC)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([F:19])=[O:9])[C:4](=[O:11])[O:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 86620466[(4R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid (100 mg, 0.6 mmol) in CH2Cl2 (2 mL) was added (diethylamino)sulfur trifluoride (DAST) (111 mg, 0.7 mmol) at 0° C. and the resulting solution was stirred at 0° C. for 1 h. More CH2Cl2 (10 mL) was added. The whole mixture was washed with cold water twice, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to afford the title compound. 1H NMR (400 MHz, CDCl3): δ4.68-4.71 (m, 1H), 3.11-3.17 (m, 1H), 2.98-3.04 (m, 1H), 1.64 (s, 3H), 1.58 (s, 3H).

Workup

  1. washThe whole mixture was washed with cold water twice
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-71c47a24fc934ff2a83a5a3846fc8856
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

Loading…