Iodoethane → HCID 86090154, compound

HRID 2100608Notes

Reaction equation

HRID 2100608 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:8](=[O:16])[O:7][CH:6]2[OH:17])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH3:26]>CN(C=O)C.Cl>[CH2:1]([C:3]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[C:9]([C:8]([O:7][CH2:25][CH3:26])=[O:16])=[C:5]([CH:6]=[O:17])[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69055625HCID 69055625, compound

Product 1

HCID 86090154HCID 86090154, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-5-ethyl-3-hydroxy-7-(trifluoromethyl)isobenzofuran-1 (3H)-one (1.97 g, 8.0 mmol) in 20 mL of DMF was added potassium carbonate (4.42 g, 32.0 mmol) followed by iodoethane (1.92 mL, 24.0 mmol). The resulting mixture was allowed to stir at ambient temperature for 1 h. The reaction was diluted with 1N HCl to pH ˜4 and extracted with EtOAc. The organics were washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (elution with 10% EtOAc/hexane) to afford 1.8 g (83%) of the title compound. 1H NMR (CDCl3): δ 10.05 (s, 1H), 7.92 (s, 1H), 7.73 (s, 1H), 4.47 (q, 2H), 2.80 (q, 2H), 1.38 (t, 3H), 1.29 (t, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with 1N HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (elution with 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-1cd6f9cc076249dbbfd8797c197129fd
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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