Methanol → HCID 68585446, compound

HRID 931826Notes

Reaction equation

HRID 931826 reaction equation
[Br:1][C:2]1[C:11]([CH:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:25])=[N+:7]2[O-].C(OC(=O)C)(=[O:28])C.CO>C(O)(=O)C>[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:25][OH:28])=[N:7]2

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 66631443HCID 66631443, compound

Product 1

HCID 68585446HCID 68585446, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide (497 mg, 1.21 mmol) in acetic acid (12 mL) was heated at 80° C. for 15 minutes. To the solution was added acetic anhydride (1.37 mL, 14.5 mmol) and the resulting solution was heated at 110° C. for 2 hours. The reaction mixture was cooled to 50° C. and methanol (6 mL) was added and stirred for 1 hour. The reaction was cooled to room temperature and concentrated. The resultant oil was taken up in tetrahydrofuran (20 mL) to which was added 6 M potassium hydroxide (20 mL) and stirred for 1 hour. The product was extracted with ethyl acetate and the organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow oil (366 mg, 74%). LCMS-ESI+ (m/z):

Workup

  1. temperatureThe reaction mixture was cooled to 50° C.
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. additionwas added 6 M potassium hydroxide (20 mL)
  5. stirringstirred for 1 hour
  6. extractionThe product was extracted with ethyl acetate
  7. concentrationthe organic layer was concentrated
  8. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dd6c2830348141639b58fbe7c3cf1531
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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