Ethanol → HCID 71062804, compound

HRID 1506785Notes

Reaction equation

HRID 1506785 reaction equation
CS(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.[CH2:27](O)[CH3:28]>>[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][CH2:27][CH3:28])=[O:25])([CH2:18][C:19]([F:20])([F:21])[F:22])[CH2:11][CH2:10]2

Participants

4

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 71063083HCID 71063083, compound

Product 1

HCID 71062804HCID 71062804, compoundYield 56%

Procedure

Methane sulfonic acid (12 mL) was added to a solution of 1E (8 g, 26.5 mmol) in ethanol (50 mL), and the mixture was stirred at room temperature for 12 h. Ethanol was removed from reaction mixture under reduced pressure, and the residue was diluted with ethyl acetate and washed with brine solution. The organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 20% ethyl acetate in hexanes to give the title compound (6 g, 56%) as a syrup. 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J=9.2 Hz, 1H), 6.75 (dd, J1=2.4 Hz, J2=8.8 Hz, 1H), 6.64 (d, J=2.4 Hz, 1H), 4.1 (q, J=6.8 Hz, 2H), 3.0-2.8 (m, 4H), 2.62-2.5 (m, 2H), 2.4 (m, 1H), 2.3 (m, 1H), 1.23 (t, J=7.2 Hz, 3H). ESI-MS m/z: 331 (M+H)+.

Workup

  1. customEthanol was removed from reaction mixture under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with brine solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-051b28aff581435bb44622f86b43df18
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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