Water → HCID 59355980, compound

HRID 660975Notes

Reaction equation

HRID 660975 reaction equation
[CH2:1]([C:3]([C:8]1[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1)([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2].[C:16]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:16][O:14][C:13]([C:11]1[S:12][C:8]([C:3]([CH2:4][CH3:5])([CH2:6][OH:7])[CH2:1][CH3:2])=[CH:9][CH:10]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67484805HCID 67484805, compound

Product 1

HCID 59355980HCID 59355980, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(1-ethyl-1-hydroxymethyl-propyl)-thiophene-2-carboxylic acid (0.750 g, 3.28 mmol) in DMF (16.0 mL) is treated with K2CO3 (0.684 g, 6.00 mmol), iodomethane (0.27 mL, 4.34 mmol), and stirred at rt overnight. The mixture is poured into H2O (30 mL) and extracted with EtOAc (3×30 mL). The combined extracts are washed with H2O, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 5-(1-ethyl-1-hydroxymethyl-propyl)-thiophene-2-carboxylic acid methyl ester (0.571 g, 72%) as a clear syrup. MS (ES): 243.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined extracts are washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 75% EtOAc

Sources & evidence

ORD record
ord-a6003d5dde404144b0da55033520b89d
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

Loading…