Dimethyl Sulfate → Tectochrysin

HRID 1292220Notes

Reaction equation

HRID 1292220 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:17][C:16]3[CH:15]=[C:14]([OH:18])[CH:13]=[C:12]([OH:19])[C:11]=3[C:9](=[O:10])[CH:8]=2)=[CH:5][CH:6]=1.S(OC)(O[CH3:24])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:24][O:18][C:14]1[CH:15]=[C:16]2[O:17][C:7]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)=[CH:8][C:9](=[O:10])[C:11]2=[C:12]([OH:19])[CH:13]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 5281607Chrysin

Product 1

HCID 5281954Tectochrysin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from chrysin by warming with one equivalent of dimethyl sulphate in DMF with finely ground K2CO3. Fine, light yellow needles, mp 175°-180° C. (lit. 163° C.). 1H NMR δ (DMSO-d6) 3.87 (s,OCH3), 6.39 (d, J=1.7 Hz, H-6), 6.80 (d, J=1.7 Hz, H-8). 7.02 (s,H-3), 7.58 (dd, J=J'=7.8 Hz, H-3'/5'), 7.60 (tt, J≈7.8 Hz, H-4'), 8.09 (d,J=7.8 Hz, H-2'/6'), 12.80 (s, C-5-OH).

Workup

  1. customlight yellow needles, mp 175°-180° C. (lit. 163° C.)

Sources & evidence

ORD record
ord-54e5b1aedddd4974bbe8841ea56f34da
Source dataset
uspto-grants-1998_05
Patent number
US05756538

Reaction notes

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