Methyl iodide → HCID 67076777, compound

HRID 2405283Notes

Reaction equation

HRID 2405283 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[C:7]([O:21][C:22](=O)C)[CH:6]=1)C.CC(C)([O-])C.[K+].C(=O)([O-])[O-].[K+].[K+].IC>CO>[CH3:1][O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[C:7]([O:21][CH3:22])[CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 670767713-Acetoxy-4-(2-m-tolyl-ethoxy)-benzoic acid ethyl ester

Product 1

HCID 67076777HCID 67076777, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of step 2 (150 mg, 0.438 mmol) was dissolved in methanol (3 ml), potassium tert-butoxide (73 mg, 0.657 mmol) was added and the mixture was stirred overnight under reflux. Potassium carbonate (60 mg, 0.44 mmol) and iodomethane (124 mg, 0.876 mmol) were then added repeatedly, at intervals of 1 h, with stirring under reflux until completion of the reaction. The volatiles were evaporated in vacuo, the residue was partitioned between EA and 2 N hydrochloric acid, and the aqueous phase was extracted with EA. The combined organic phases were dried over sodium chloride, decanted and evaporated to dryness to yield the title compound.

Workup

  1. temperatureunder reflux
  2. stirringwith stirring
  3. temperatureunder reflux until completion of the reaction
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue was partitioned between EA and 2 N hydrochloric acid
  6. extractionthe aqueous phase was extracted with EA
  7. dry with materialThe combined organic phases were dried over sodium chloride
  8. customdecanted
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-747691e2221f412d8a817b68b5758ece
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

Loading…