Hydrochloric Acid → HCID 12179942, compound

HRID 1987674Notes

Reaction equation

HRID 1987674 reaction equation
[CH2:1]([O:4][C@H:5]1[CH2:10][O:9]C(C)(C)[O:7][C@H:6]1[CH:13]=[CH2:14])C=C.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[OH:9][CH2:10][C@H:5]1[C@@H:6]([OH:7])[CH:13]=[CH:14][CH2:1][O:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57723932HCID 57723932, compound

Product 1

HCID 12179942HCID 12179942, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cis-5-allyloxy-2,2-dimethyl-4-vinyl-[1,3]dioxane (50 mg, 0.29 mmol) in MeOH (5 mL) was added a solution of methanolic HCl (0.5 mL, prepared from 0.5 mL conc. HCl in 30 mL of MeOH). The mixture was stirred for 30 min at ambient temperature. Aqueous saturated NaHCO3 (5 mL) was added and the mixture was diluted with EtOAc (50 mL). The organic layer was washed with saturated NaHCO3 (30 mL). The aqueous layer was washed with EtOAc (30 mL×2). The combined organic layers were dried over Na2SO4, concentrated in vacuo, and the residue was purified by flash chromatography with 100% EtOAc

Workup

  1. washThe organic layer was washed with saturated NaHCO3 (30 mL)
  2. washThe aqueous layer was washed with EtOAc (30 mL×2)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-01db95d0c7ac4f07a138e32adc82f34a
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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