Potassium Carbonate → HCID 20253978, compound

HRID 638255Notes

Reaction equation

HRID 638255 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28]>[I-].[K+].CC(=O)CC>[C:27]([C:23]1[S:24][CH:25]=[CH:26][C:22]=1[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1)([O:29][CH3:30])=[O:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylateHCID 20253981HCID 20253981, compound

Product 1

HCID 20253978HCID 20253978, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred suspension of 8.0 g of 4-(4-hydroxyphenyl)pentanol, 18.41 g of anhydrous potassium carbonate, 0.4 g of potassium iodide, 10.44 g of methyl 3-bromomethyl-2-thiophenecarboxylate, and 225 ml of 2-butanone was heated under reflux overnight, with exclusion of moisture. The mixture was filtered while hot and the filter cake was washed with 2-butanone. The combined filtrate was concentrated, and a solution of the residue and dichloromethane was washed with 10% sodium hydroxide solution, water and saturated brine. The dried (over anhydrous sodium sulfate) organic phase was filtered and the filtrate was concentrated to an oil. Purification by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; two silica gel columns; 0.2 l/min flow rate; Gow Mac model 80-800 UV detector; 30% V/V ethyl acetate in hexane) gave 11.23 g (75.6%) of product as an oil, dried at 60° C. for 2 hours.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight, with exclusion of moisture
  3. filtrationThe mixture was filtered while hot and the filter cake
  4. washwas washed with 2-butanone
  5. concentrationThe combined filtrate was concentrated
  6. washa solution of the residue and dichloromethane was washed with 10% sodium hydroxide solution, water and saturated brine
  7. dry with materialThe dried (over anhydrous sodium sulfate) organic phase
  8. filtrationwas filtered
  9. concentrationthe filtrate was concentrated to an oil
  10. customPurification by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; two silica gel columns; 0.2 l/min flow rate; Gow Mac model 80-800 UV detector; 30% V/V ethyl acetate in hexane)

Sources & evidence

ORD record
ord-de64db3e55c74f89905ab8f000887e53
Source dataset
uspto-grants-1985_12
Patent number
US04560701

Reaction notes

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