Water → HCID 59286719, compound

HRID 2196091Notes

Reaction equation

HRID 2196091 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3([O:15][C:7]=2[C:6]([C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1)[CH2:14][CH2:13][S:12][CH2:11]3.[C:19]([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:15][C:7]=2[C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1)[CH2:14][CH2:13][S:12][CH2:11]3

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 59286721HCID 59286721, compound

Product 1

HCID 59286719HCID 59286719, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 7-methoxy-4′,5′-dihydro-spiro[1,3-benzodioxole-2,3′-(2H)-thiophen]-4-carboxylic acid (161 mg, 0.600 mmol), K2CO3 (166 g, 1.20 mmol) and dimethyl sulphate (74 μL, 0.78 mmol) in acetone (1 mL) was kept at 50° C. overnight. At room temperature water (15 mL) was added and the aqueous phase was extracted with ethyl acetate (2×20 mL). The organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard HPLC purification afforded compound 505 (24 mg, 14%). 1H NMR (CDCl3) δ 7.44 (d, 1H), 6.56 (d, 1H), 3.94 (s, 3H), 3.88 (s, 3H), 3.32 (d, 1H), 3.24 (d, 1H), 3.05 (t, 2H), 2.49 (td, 2H).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated to dryness under reduced pressure
  4. customStandard HPLC purification

Sources & evidence

ORD record
ord-a9d686f64d3d4a19b920426cff07474e
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

Loading…