Sodium Bicarbonate → HCID 135736099, compound

HRID 1921270Notes

Reaction equation

HRID 1921270 reaction equation
O1CCCCC1[O:7][C:8]1[CH:30]=[CH:29][C:11]2[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C4CCCCO4)=[CH:18][CH:17]=3)=[N:13][O:14][C:10]=2[CH:9]=1.C([O-])(O)=O.[Na+]>CO>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:12]2[C:11]3[CH:29]=[CH:30][C:8]([OH:7])=[CH:9][C:10]=3[O:14][N:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23117142HCID 23117142, compound

Product 1

HCID 135736099HCID 135736099, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(tetrahydro-2H-pyran-2-yloxy)-3-[4-(tetrahydro-2H-pyran-2-yloxy)benzyl]-1,2-benzisoxazole (3.85 mmol) and paratoluenesulfonic acid (APTS, catalytic amount) were dissolved in methanol (20 ml). After reaction at 60-70° C. for 3 h, the reaction mixture was cooled to room temperature and poured into satured NaHCO3 and extracted with EtOAc. After washing (H2O) and drying (MgSO4), the extract was concentrated. The crude product was purified by flash chromatography (toluene/1,4-dioxane 8/2) and crystallised to give an off-white crystal (0.58 g, 31%). mp 178° C.

Workup

  1. customAfter reaction at 60-70° C. for 3 h
  2. extractionextracted with EtOAc
  3. washAfter washing (H2O)
  4. dry with materialdrying (MgSO4)
  5. concentrationthe extract was concentrated
  6. customThe crude product was purified by flash chromatography (toluene/1,4-dioxane 8/2)
  7. customcrystallised

Sources & evidence

ORD record
ord-f7cff88c76a247a3a992c0e547695fc0
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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