Sodium Bicarbonate → HCID 11435650, compound

HRID 1492314Notes

Reaction equation

HRID 1492314 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:18][CH2:17][CH2:16][C:11]21OCC[O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CC(C)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:18][CH2:17][CH2:16][C:11]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 131303736-[(Benzyloxy)methyl]-1,4-dioxaspiro[4.4]nonane

Product 1

HCID 11435650HCID 11435650, compoundYield 136.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 4 (7.95 g, 32.0 mmol) and p-toluenesulfonic acid monohydrate (0.30 g, 1.58 mmol) in acetone (160 mL) was stirred at ambient temperature for 100 min. The mixture was neutralized with NaHCO3 solution and acetone was evaporated under reduced pressure. The residue was diluted with water and extracted with EtOAc. The combined organic layers were washed with NaCl solution and dried over Na2SO4. Filtration and concentration gave 8.94 g of an oily material, which was purified by column chromatography (SiO2 gel 50 g EtOAc in n-hexane 5-10%), to give 5.83 g (89.2%) of 5, as a pale yellow oil.

Workup

  1. customwas evaporated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1c5063a001ae42de9983a66cc008abff
Source dataset
uspto-grants-1994_12
Patent number
US05373004

Reaction notes

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