Iodoethane → HCID 89995591, compound

HRID 523092Notes

Reaction equation

HRID 523092 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].I[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 89995593HCID 89995593, compound

Product 1

HCID 89995591HCID 89995591, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3-hydroxy-4-nitrophenyl)(3-methoxyazetidin-1-yl)methanone (Preparation 115, 250 mg, 1.007 mmol), iodoethane (185 mg, 1.208 mmol) and potassium carbonate (278 mg, 2.014 mmol) in DMF (10 mL) was stirred at room temperature for 2 hours. The reaction was filtered and the filtrate diluted with ethyl acetate (60 mL). The organic phase was washed with water (20 mL×2), brine (20 mL) and dried over sodium sulphate. The solvent was concentrated in vacuo and the residue purified by silica gel column chromatography eluting with 20% hexane in ethyl acetate to afford the title compound as a yellow powder (230 mg, 84%).

Workup

  1. filtrationThe reaction was filtered
  2. additionthe filtrate diluted with ethyl acetate (60 mL)
  3. washThe organic phase was washed with water (20 mL×2), brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationThe solvent was concentrated in vacuo
  6. customthe residue purified by silica gel column chromatography
  7. washeluting with 20% hexane in ethyl acetate

Sources & evidence

ORD record
ord-db09a98423e64b149e94fecdbf7d7767
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

Loading…