Potassium Carbonate → HCID 59286715, compound

HRID 2196103Notes

Reaction equation

HRID 2196103 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].Br[CH2:16][C:17]1([CH2:25]Br)[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:7][O:6][C:4]([C:3]1[C:2]2[O:1][CH2:25][C:17]3([CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19][CH2:18]3)[CH2:16][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 145372285,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 59286715HCID 59286715, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure, dialkylation of compound 513 (1.19 g, 6 mmol) with compound 521 (2.0 g, 6.62 mmol) in DMSO (30 mL) in the presence of K2CO3 (2.07 g, 15 mmol) afforded compound 522 as a white solid material after purification by column chromatography (30-40% EtOAc in light petroleum). LC-MS: RT=2.99 min.; m/z 339.31 (M+H)+, 361.25 (M+Na)+. 1H NMR (CDCl3): δ 7.45 (1H, d, J 8.8), 6.59 (1H, d, J 8.8), 4.22 (2H, s), 4.18 (2H, s), 3.89 (3H, s), 3.86 (7H, s), 1.43 (6H, s).

Sources & evidence

ORD record
ord-af24c399ca0e4bd591233c4b5ea55400
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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