Water → HCID 90004151, compound

HRID 587860Notes

Reaction equation

HRID 587860 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([OH:14])=[O:13])[CH2:3]1.[C:15]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7000055HCID 7000055, compound

Product 1

HCID 90004151HCID 90004151, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To the stirred solution of (R)-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (5.0 g, 26.3 mmol), K2CO3 (10.90 g, 79 mmol) and methyl iodide (6.58 mL, 105 mmol) was added in DMF (50 mL) and stirred for overnight at 25° C. Water was added (130 mL) and extracted with ethyl acetate (2×30 mL). The organic phase was washed with aq. Sodium bicarbonate solution (2×20 mL), dried over Na2SO4 and filtered. The clear organic phase was evaporated in vacuo to get pure title compound (4.5 g) m/z 204.09.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe organic phase was washed with aq. Sodium bicarbonate solution (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe clear organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-5310ee237e75452691b153ae6b039a54
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

Loading…