Hydrochloric Acid → HCID 12179941, compound

HRID 1987675Notes

Reaction equation

HRID 1987675 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 68841397HCID 68841397, compound

Product 1

HCID 12179941HCID 12179941, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-5-allyloxy-2,2-dimethyl-4-vinyl-[1,3]dioxane (48 mg, 0.28 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 washed with brine, 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. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-ea9206175c8b4a4199ae780d9f4779f5
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

Loading…