Potassium Carbonate → Methyl [4-(prop-1-yloxycarbonyl)-3-thienyl]acetate

HRID 256556Notes

Reaction equation

HRID 256556 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[C:11]([C:14]1[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][S:17][CH:18]=1)([OH:13])=[O:12]>CN(C=O)C.O>[CH2:8]([O:13][C:11]([C:14]1[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][S:17][CH:18]=1)=[O:12])[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 14326173Methyl (4-carboxy-3-thienyl)acetate

Product 1

HCID 54180130Methyl [4-(prop-1-yloxycarbonyl)-3-thienyl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (670 mg) and, after 15 minutes, 1-iodopropane (0.26 ml) were added successively to a stirred solution of methyl (4-carboxy-3-thienyl)acetate (490 mg) in DMF (10 ml). After 3 h, the resulting mixture was diluted with water and extracted with ether. The extracts were washed with water, dried, and concentrated to give methyl [4-(prop-1-yloxycarbonyl)-3-thienyl]acetate (600 mg, quantitative yield) as a yellow liquid, pure by GC, IR (film): 1735, 1710 cm-1, 1H nmr: delta 1.00 (3H, t), 1.75 (2H, q), 3.69 (3H, s), 3.92 (2H, s), 4.20 (2H, t), 7.13 (1H, d J 3.5 Hz), 8.12 (1H, d J 3.5 Hz) ppm.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8fef5407884f46e3af0207d692202bf3
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Reaction notes

Loading…