Water → HCID 89874785, compound

HRID 715419Notes

Reaction equation

HRID 715419 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=[C:4]([CH:14]=O)[CH:3]=1.[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].O.CCOC(C)=O>C1COCC1.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[CH3:16][C:17]([S@:20](/[N:22]=[CH:14]/[C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=1)=[O:21])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 89875399HCID 89875399, compound

Product 1

HCID 89874785HCID 89874785, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-methyl-5-(2,2,2-trifluoroethoxy)picolinaldehyde (1.6 g, 7.3 mmol, Step-5), (R)-2-methylpropane-2-sulfinamide (1.33 g, 11.0 mmol), and titanium tetraethoxide (2.50 g, 11.0 mmol) in THF (30 mL) is refluxed with stirring for 2 hours. After cooling to 0° C., water (30 mL) and EtOAc (80 mL) are added to the mixture, and this is filtered through a pad of Celite. The filtrate is washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica-gel eluting with n-hexane/EtOAc (4:1-2:1) to give 1.14 g (48% yield) of the title compound as a pale yellow solid.

Workup

  1. temperatureis refluxed
  2. filtrationthis is filtered through a pad of Celite
  3. washThe filtrate is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica-gel
  7. washeluting with n-hexane/EtOAc (4:1-2:1)

Sources & evidence

ORD record
ord-2d93cb1572ef4dd1a3c1bfbbe4fc715a
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…