Potassium Carbonate → HCID 58506477, compound

HRID 2167294Notes

Reaction equation

HRID 2167294 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3:13])([CH3:12])[O:7][C:6]=2[CH:14]=1.CC1C=CC(S(O[CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH3:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3:12])([CH3:13])[O:7][C:6]=2[CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 105839507-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-oneHCID 11076628HCID 11076628, compound

Product 1

HCID 58506477HCID 58506477, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 7-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one, (19.4 g, 100 mmol), 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate (27.4 g, 100 mmol) and K2CO3 (41 g, 300 mmol) in CH3CN (500 mL) was refluxed for 4.5 hours. The mixture was poured in H2O (1000 mL) and extracted twice with CH2Cl2 (500 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (PE/EtOAc=9/1) to give the title compound (22 g) as white solid. LC-MS (ES, m/z): 297 [M+H]+.

Workup

  1. extractionextracted twice with CH2Cl2 (500 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (PE/EtOAc=9/1)

Sources & evidence

ORD record
ord-e25fa1284d644f03bfe4e53ad0641e4b
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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