Potassium Carbonate → 9-Methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dioxane]-6-carboxylic acid methyl ester

HRID 2196104Notes

Reaction equation

HRID 2196104 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([CH2:23]Br)[CH2:22][O:21][CH2:20][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][CH2:23][C:17]3([CH2:22][O:21][CH2:20][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 124581345,5-Bis(bromomethyl)-1,3-dioxane

Product 1

HCID 592867099-Methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dioxane]-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure, dialkylation of compound 513 (198 mg, 1 mmol) with compound 523 (301 mg, 1.1 mmol) in DMSO (5 mL) in the presence of K2CO3 (345 mg, 2.5 mmol) afforded compound 524 as a white solid material after purification by column chromatography (50-65% EtOAc in light petroleum). LC-MS: RT=2.65 min.; m/z 311.23 (M+H)+. 1H NMR (DMSO-d6): 7.37 (1H, d, J 8.8), 6.81 (1H, d, J 8.8), 4.80 (1H, d, J 6.4), 4.78 (1H, d, J 6.4), 4.07 (2H, s), 4.01 (2H, s), 3.81 (7H, s), 3.76 (3H, s).

Sources & evidence

ORD record
ord-92ae7b2fde4a4815ae7d851bbced86b3
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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