Methanol → HCID 78003675, compound

HRID 1506799Notes

Reaction equation

HRID 1506799 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:12]([CH2:23][C:24]([OH:26])=[O:25])([CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:11][CH2:10]2.[CH3:27]O>>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:12]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:18][C:19]([F:20])([F:21])[F:22])[CH2:11][CH2:10]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 71063083HCID 71063083, compound

Product 1

HCID 78003675HCID 78003675, compoundYield 91%

Conditions

Temperature
80 °C

Procedure

Sulfuric acid (2 mL) was added to a solution of 1E (8.5 g, 28.1 mmol) in methanol (80 mL), and the mixture was stirred at 80° C. for 3 h. Methanol was removed from reaction mixture under reduced pressure, and the residue was diluted with ethyl acetate and extracted with saturated NaHCO3 solution and brine solution. The organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give the title compound (8.5 g, 91%) as a syrup. 1H NMR (400 MHz, DMSO-d6) δ 10.43 (s, 1H), 7.77 (d, J=8.6 Hz, 1H), 6.75 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 6.65 (s, 1H), 3.57 (s, 3H), 3.05-2.78 (m, 4H), 2.73-2.55 (m, 2H), 2.32 (m, 1H), 2.09 (m, 1H). ESI-MS m/z: 317 (M+H)+.

Workup

  1. customMethanol was removed from reaction mixture under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. extractionextracted with saturated NaHCO3 solution and brine solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b11c9b12fb314df0b39b9cc4173ae9a6
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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