Water → HCID 11780118, compound

HRID 2191044Notes

Reaction equation

HRID 2191044 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]2[C@@H:11]1[O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:18].[Na+].O>C(O)CO>[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]([OH:12])[C@@H:11]1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5235Sodium FluorideHCID 86641125HCID 86641125, compound

Product 1

HCID 11780118HCID 11780118, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

Compound 35.7 (2.2 g, 9.32 mmol) was dissolved in 10 mL ethyleneglycol, and then treated with NaF (2.2 g), KHF2 (2.2 g). The mixture was stirred at 200° C. for 4 h, cooled to r.t. and then treated with water (150 mL). The aqueous mixture was extracted twice with 200 mL EtOAc. The organic extracts were combined, dried over MgSO4, filtered and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 20-100% EtOAc in hexane to give compound 35.8 (786 mg, 33% yield).

Workup

  1. temperaturecooled to r.t.
  2. extractionThe aqueous mixture was extracted twice with 200 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down under reduced pressure
  6. washeluting with 20-100% EtOAc in hexane

Sources & evidence

ORD record
ord-20c1a4c8c9ed4e1398160e656d798f82
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

Loading…