Water → HCID 18463960, compound

HRID 2230919Notes

Reaction equation

HRID 2230919 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1.[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:17][O:15][C:14]([C:12]1[S:13][C:9]([CH2:8][CH2:7][CH2:6][CH:2]2[O:3][CH2:4][CH2:5][O:1]2)=[CH:10][CH:11]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11831596HCID 11831596, compound

Product 1

HCID 18463960HCID 18463960, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-[1,3-dioxolan-2-yl]propyl)-2-thiophene carboxylic acid (58.0 g, 239 mmol) in 300 mL of dimethylformamide was added potassium carbonate (41.4 g, 299 mmol) followed by methyl iodide (51.0 g, 359 mmol). The slurry was stirred at ambient temperature for 17 hours and then poured into 600 mL of water. The resulting suspension was extracted twice with 500 mL of t-butylmethylether and the combined extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated by rotory evaporation to afford 57.84 g (94.3%) of the title compound which was of sufficient purity for use in Preparation 3. IR (CHCl3, cm−1) 3021, 1707, 1541, 1463, 1296, 1101. 1H NMR (300 MHz, CDCl3) d 1.75 (m, 4H), 2.84 (t, J=7.4 Hz, 2H), 3.81 (s, 3H), 3.82 (m, 2H), 3.92 (m, 2H), 4.84 (t, J=4.3 Hz, 1H), 6.76 (d, J=3.9 Hz, 1H), 7.58 (d, J=3.7 Hz, 1H).

Workup

  1. extractionThe resulting suspension was extracted twice with 500 mL of t-butylmethylether
  2. washthe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotory evaporation

Sources & evidence

ORD record
ord-c6cee1eae9fe4edd8c289b7891cb4d32
Source dataset
uspto-grants-2002_07
Patent number
US06426417B1

Reaction notes

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