Dimethyl Sulfoxide → HCID 67820121, compound

HRID 359041Notes

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 mol) of 3-bromo-3,4-dihydro-2,2-dimethyl-7-methoxy-6-(p-tolylsulfonyl)-2H-benzo [b]pyran-4ol are dissolved in 32 ml of dimethyl sulfoxide, 4.9 g of valerolactam (0.0526 mol) and 0.8 g (0.033 mol) of NaH, 80 % suspension in oil, are added and the mixture is stirred for 5 hours at 40° C., poured on ice water and filtered with suction. The residue is boiled up several times with methanol. White crystals of melting point 261-63° C.

Workup

additionpoured on ice water
filtrationfiltered with suction

Sources & evidence

ORD record: ord-3b77289082bb461991cc2d78a674be6f
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999371

Reaction notes

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