Potassium Carbonate → HCID 59286725, compound

HRID 2196101Notes

Reaction equation

HRID 2196101 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(C)C=CC(S(O[CH2:25][C:26]2([CH2:32]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:7][O:6][C:4]([C:3]1[C:2]2[O:1][CH2:32][C:26]3([CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH2:25][O:12][C:11]=2[C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11694090Methyl 2,3-dihydroxy-4-methoxybenzoateHCID 59286720HCID 59286720, compound

Product 1

HCID 59286725HCID 59286725, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure, dialkylation of compound 513 (95 mg, 0.48 mmol) with compound 519 (240 mg, 0.53 mmol) in DMSO (3 mL) in the presence of K2CO3 (166 mg, 1.2 mmol) afforded compound 520 as a white solid material after purification by column chromatography (45-65% EtOAc in light petroleum). LC-MS: RT=2.40 min.; 1H NMR (DMSO-d6): δ 7.34 (1H, d, J 8.8), 6.78 (1H, d, J 8.8), 3.99 (4H, s), 3.80 (3H, s), 3.76 (3H, s), 3.61 (4H, t, J 5.5), 1.54 (4H, t, J 5.5).

Sources & evidence

ORD record
ord-bec318af90634171b03a1ee7eaacf23b
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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