Methyl Methanesulfonate → HCID 19940147, compound

HRID 1493519Notes

Reaction equation

HRID 1493519 reaction equation
C([Li])CCC.[CH3:6][S:7]([O:10][CH3:11])(=[O:9])=[O:8].[CH:12]([C:14]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[NH:16][C:15]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=O.[O:29]1CCC[CH2:30]1>>[CH3:6][S:7]([O:10][CH3:11])(=[O:9])=[O:8].[OH:29][CH2:30][CH:12]([C:14]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[NH:16][C:15]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[S:7]([CH3:6])(=[O:9])=[O:10]

Participants

6

Reactant 4

HCID 4156Methyl MethanesulfonateHCID 8028Tetrahydrofuran2×HCID 19940143HCID 19940143, compoundHCID 178418339Butyllithium

Product 2

HCID 4156Methyl MethanesulfonateHCID 19940147HCID 19940147, compoundYield 43%

Conditions

Temperature
-78 °C

Procedure

The lithio derivative of methyl methanesulfonate was prepared at -78° C. under argon by the dropwise addition of 0.56 mL of a 1.60M n-butyllithium (0.891 mmol) to a solution of 72 μL (0.85 mmol) of methyl methanesulfonate in 2 mL of anhydrous tetrahydrofuran. After 45 minutes at -78° C., 3-formyl-2,5-dithienylpyrrole (105 mg, 0.41 mmol) in 1 mL of tetrahydrofuran was added dropwise over a 5 minute period to the lithio methyl methanesulfonate solution. The reaction mixture was allowed to stir for 30 minutes at -78° C. After the completion of reaction, it was then quenched with a saturated aqueous ammonium chloride solution. The aqueous layer was extracted three times with 50 mL portions of ethyl acetate and the combined organic layers were washed with water (10 mL×1) and brine (10 mL×1). The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified on 50 g of silica gel. Elution with hexane-ethyl acetate (5:1), gave 64 mg (43%) of title compound.

Workup

  1. customAfter the completion of reaction, it
  2. customwas then quenched with a saturated aqueous ammonium chloride solution
  3. extractionThe aqueous layer was extracted three times with 50 mL portions of ethyl acetate
  4. washthe combined organic layers were washed with water (10 mL×1) and brine (10 mL×1)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified on 50 g of silica gel
  9. washElution with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-5627ddad66b1499f80abeec647dd1a04
Source dataset
uspto-grants-1991_06
Patent number
US05021586

Reaction notes

Loading…