Hydrochloric Acid → HCID 12897670, compound

HRID 2191011Notes

Reaction equation

HRID 2191011 reaction equation
[CH3:1][C:2]1([CH3:20])[O:6][CH:5]2[O:7][CH:8]([CH2:10][O:11]C(=O)C3C=CC=CC=3)[CH2:9][CH:4]2[O:3]1.C[O-].[Na+].Cl>CO>[CH3:1][C:2]1([CH3:20])[O:6][CH:5]2[O:7][CH:8]([CH2:10][OH:11])[CH2:9][CH:4]2[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 14757118HCID 14757118, compound

Product 1

HCID 12897670HCID 12897670, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 9.4 (11.0 g, 39.6 mmol) in MeOH (100 mL) at 0° C. was treated with NaOMe (4.3 M in MeOH, 3 mL, 20 mmol) and stirred for 30 min. The mixture was warmed to ambient temperature and stirred for 1 h. The mixture was cooled to 0° C. and treated with 1 N HCl (10 mL) then concentrated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and stirred for 30 minutes, dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to a silica gel column chromatography (SiO2, 4×20 cm, 20-50% EtOAc-hexanes gradient) to afford compound 9.5 (4.1 g, 60% yield).

Workup

  1. stirringstirred for 1 h
  2. temperatureThe mixture was cooled to 0° C.
  3. concentrationthen concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. stirringstirred for 30 minutes
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ce6f56b99914929b58dfd15129db2d2
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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