(Diethylamino)sulfur trifluoride → 2-(3-(alpha-Fluorobenzyl)phenyl)-[1,3]-dioxolane

HRID 1666783Notes

Reaction equation

HRID 1666783 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)O)[CH:9]=[CH:10][CH:11]=1.C(N(S(F)(F)[F:26])CC)C>ClCCl>[F:26][CH:12]([C:8]1[CH:7]=[C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)[CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10824966(3-[1,3]Dioxolan-2-ylphenyl)phenylmethanol

Product 1

HCID 210714122-(3-(alpha-Fluorobenzyl)phenyl)-[1,3]-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Combine (3-[1,3]-dioxolan-2-ylphenyl)phenylmethanol (2.3 g, 8.9 mmol) and dichloromethane (50 ml). Cool to about −78° C. Add dropwise a solution of (diethylamino)sulfur trifluoride (1.7 ml, 12.9 mmol). After 10 minutes, quench with water and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 7:3 hexane:EtOAc to give the title compound.

Workup

  1. customquench with water
  2. extractionextract with dichloromethane
  3. washwash sequentially with distilled water and brine
  4. dry with materialdry (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give a residue
  8. washChromatograph the residue eluting with 7:3 hexane

Sources & evidence

ORD record
ord-7ce8b06cc6c04105a234c4d3671baf02
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

Loading…