Ethanol → HCID 71062779, compound

HRID 1506794Notes

Reaction equation

HRID 1506794 reaction equation
CS(O)(=O)=O.[CH2:6]([C:8]1([CH2:20][C:21]([OH:23])=[O:22])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[C:9]1=[O:19])[CH3:7].[CH2:24](O)[CH3:25]>>[CH2:6]([C:8]1([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[C:9]1=[O:19])[CH3:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 71062920HCID 71062920, compound

Product 1

HCID 71062779HCID 71062779, compoundYield 72%

Procedure

Methane sulfonic acid (5 mL) was added to a solution of 4B (5 g, 20.16 mmol) in ethanol (50 mL), and the mixture was stirred at room temperature for 16 h. Ethanol was removed under reduced pressure, and the residue was diluted with ethyl acetate and washed with saturated NaCl solution. The organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under vacuum to afford the title compound (4 g, 72%) as a solid. 1H NMR (300 MHz, CDCl3): δ 7.92 (d, J=8.7 Hz, 1H), 6.86 (bs, 1H), 6.7 (dd, J1=2.4 Hz, J2=8.7 Hz, 1H), 6.61 (d, J=2.1 Hz, 1H), 4.08 (q, J=7.2 Hz, 2H), 3.1-2.9 (m, 2H), 2.77 (dt, J1=16.9 Hz, J2=4.5 Hz, 1H), 2.5-2.35 (m, 2H), 2.02 (dt, J1=13.5 Hz, J2=4.8 Hz, 1H), 1.8-1.58 (m, 2H), 1.2 (t, J=7.2 Hz, 3H), 0.9 (t, J=7.5 Hz, 3H). ESI-MS m/z=275 (M−H)−.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated NaCl solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f0515f2d44204148a5c69d82bcdb128a
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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