Hydrochloric Acid → HCID 19914035, compound

HRID 1090852Notes

Reaction equation

Cl.[Na].[C:3]([C:11]1[N:12]([CH2:16][CH2:17][CH:18]2[C:23](=[O:24])[O:22][C:21](C)(C)[O:20][C:19]2=[O:27])[CH:13]=[CH:14][CH:15]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:28]O>>[C:3]([C:11]1[N:12]([CH2:16][CH2:17][CH:18]([C:23]([O:22][CH3:21])=[O:24])[C:19]([O:20][CH3:28])=[O:27])[CH:13]=[CH:14][CH:15]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol2×

HCID 5360545Sodium

HCID 109147952-Benzoyl-1-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]pyrrole

Product 1

HCID 19914035HCID 19914035, compoundYield 42%

Procedure

To a 0° C. solution of methanol (10 mL) which had been saturated with gaseous hydrogen chloride was added a solution of the sodium salt of 2-benzoyl-1-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]pyrrole (1.41 g, 3.9 mmol) in methanol (10 mL). The mixture was stirred for sixteen hours at room temperature and was then concentrated under reduced pressure. The residue was purified by chromato-graphy on silica eluting with hexane/ethyl acetate (70:30) to yield 530 mg (42%) of 2-benzoyl-1-[3,3-di(methoxycarbonyl)propyl]pyrrole.

Workup

customTo a 0° C.
concentrationwas then concentrated under reduced pressure
customThe residue was purified by chromato-graphy on silica eluting with hexane/ethyl acetate (70:30)

Sources & evidence

ORD record: ord-f476820b9bdb4d0792e37a72700cbea6
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082951

Reaction notes

Loading…