Methanol → HCID 22561682, compound

HRID 1839674Notes

Reaction equation

HRID 1839674 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].C([O:9][C:10]([C:12]1[C:16]([CH2:17][CH2:18][CH2:19]SC)=[C:15]([CH:22]=[O:23])[NH:14][C:13]=1[CH3:24])=[O:11])C.[CH3:25]O>O>[CH:22]([C:15]1[NH:14][C:13]([CH3:24])=[C:12]([C:10]([OH:11])=[O:9])[C:16]=1[CH2:17][CH2:18][CH2:19][S:3]([CH3:25])(=[O:5])=[O:2])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 20761747HCID 20761747, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22561682HCID 22561682, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Oxone (614 mg, 1 mmol) dissolved in water (2 mL) was added portionwise to a solution of 5-formyl-2-methyl-4-(3-methylsulfanyl-propyl)-1H-pyrrole-3-carboxylic acid ethyl ester (269 mg, 1 mmol) in methanol (4 mL) cooled in an ice bath. The mixture was stirred for 3 hours, keeping the temp between 0° C. and rt. The reaction was diluted with 10 mL of water, the resulted precipitate was collected by vacuum filtration, washed with water and dried to give 95 mg of the desired product. The water filtrate was extracted with ethyl acetate, dried and concentrated to give another 74 mg of the product. Total of 169 mg (56%) of 5-formyl-4-(3-methanesulfonyl-propyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester was obtained.

Workup

  1. temperaturecooled in an ice bath
  2. customthe temp between 0° C. and rt
  3. filtrationthe resulted precipitate was collected by vacuum filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-94460a2f39fa4a559194c3da86ce8d4d
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

Loading…