Hydrochloric Acid → HCID 70170377, compound

HRID 2171123Notes

Reaction equation

HRID 2171123 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13]3)=[C:6]([O:20]COC)[C:5]=1[O:24][CH3:25])[CH3:2].Cl>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:18]=2[CH2:17][CH2:16][C:15]3=[O:19])=[C:6]([OH:20])[C:5]=1[O:24][CH3:25])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86677578HCID 86677578, compound

Product 1

HCID 70170377HCID 70170377, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 5-(4-ethoxy-3-methoxy-2-(methoxymethoxy)phenyl)-2,3-dihydro-1H-inden-1-one (1 g, 2.92 mmol) in methanol (20 mL) was added conc. hydrochloric acid (3 mL) and heated to 60° C. for 1 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was basified with sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (850 mg, 97.7%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0608b02a93964298a13e7cc870ce928e
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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