Dimethyl Sulfoxide → HCID 67820121, compound

HRID 2379783Notes

Reaction equation

Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[C:11]([O:24][CH3:25])[C:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:13][C:4]=2[CH:3]1O.[C:27]1(=[O:33])[NH:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[H-].[Na+].CS(C)=[O:38]>>[CH3:8][C:7]1([CH3:9])[O:6][C:5]2[CH:10]=[C:11]([O:24][CH3:25])[C:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:15])=[O:16])=[CH:13][C:4]=2[C@@H:3]([N:32]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[O:33])[C@@H:2]1[OH:38]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 126652-Piperidone

HCID 24758Sodium hydride

HCID 14210535HCID 14210535, compound

Product 1

HCID 67820121HCID 67820121, compound

Conditions

Temperature: 40 °C

Procedure

5 g (0.011 mole) of 3-bromo-3,4-dihydro-2,2-dimethyl-7-methoxy-6-(p-tolylsulfonyl)-2H-benzo[b]pyran-4-ol are dissolved in 32 ml of dimethyl sulfoxide, and 4.9 g of valerolactam (0.0526 mole) and 0.8 g (0,033 mole) of NaH, 80% suspension in oil, are added, and the mixture is stirred at 40° C. for 5 hours. It is poured into ice-water and filtered with suction. The residue is extracted by boiling several times with methanol.

Workup

filtrationfiltered with suction
extractionThe residue is extracted

Sources & evidence

ORD record: ord-1c3fd5c22d8b4ef995f3bf14c15d678c
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364878

Reaction notes

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