Sodium Methoxide → HCID 117737100, compound

HRID 1504542Notes

Reaction equation

HRID 1504542 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[OH:29])=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:22]([C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[OH:29])[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 131734330HCID 131734330, compound

Product 1

HCID 117737100HCID 117737100, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
70 °C

Procedure

A 25-mL pressure vessel was charged with (E)-ethyl 3-(5-(benzylthio)-2-((2-hydroxycyclohexyl)amino)phenyl)acrylate (2.36 g, 5.73 mmol), methanol (10 ml), and a solution of sodium methoxide in methanol (25 wt. %, 2.64 mL, 11.47 mmol). The reaction vessel was sealed with a Teflon cap and the yellow reaction mixture was warmed to 70° C. After 16 h, additional solution of sodium methoxide in methanol (25 wt. %, 1.9 mL, 8.25 mmol) was added and the reaction vessel was sealed and warmed to 100° C. After 20 h, the reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure to furnish a yellow residue which was purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 70% EtOAc in heptane) to afford 6-(benzylthio)-1-((1R,2R)-2-hydroxycyclohexyl)quinolin-2(1H)-one (469 mg, 1.283 mmol, 22.38% yield) as a yellow syrup. m/z (ESI) 366.1 (M+H)+.

Workup

  1. customcap
  2. customthe reaction vessel was sealed
  3. temperaturewarmed to 100° C
  4. waitAfter 20 h
  5. temperatureto cool to ambient temperature
  6. concentrationconcentrated under reduced pressure
  7. customto furnish a yellow residue which
  8. customwas purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 70% EtOAc in heptane)

Sources & evidence

ORD record
ord-2f9411aadb644a30a628980c0ba9c5f5
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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