Water → HCID 59286716, compound

HRID 2196098Notes

Reaction equation

HRID 2196098 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3([O:16][C:7]=2[C:6]([C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1)[CH2:15][CH2:14][S:13][CH2:12][CH2:11]3.[C:20]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.O>CC(C)=O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3([O:16][C:7]=2[C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:5][CH:4]=1)[CH2:11][CH2:12][S:13][CH2:14][CH2:15]3

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 59286714HCID 59286714, compound

Product 1

HCID 59286716HCID 59286716, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 7-methoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylic acid (570 mg, 2.02 mmol), K2CO3 (558 mg, 4.04 mmol) and dimethyl sulphate (0.25 mL, 2.62 mmol) in acetone (14 mL) was stirred at 50° C. overnight. At room temperature water (30 mL) was added. The aqueous phase was extracted with dichloromethane (3×15 mL). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard silica gel column chromatography afforded methyl 7-methoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylate (407 mg, 68%). 13C NMR (DMSO) δ 163.8, 148.1, 146.9, 134.6, 123.4, 118.3, 107.1, 105.9, 56.1, 51.6, 35.9, 25.4.

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1090110147f342619498db3799eb0d2a
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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