Ethanol → HCID 11992477, compound

HRID 2241036Notes

Reaction equation

HRID 2241036 reaction equation
[C:1]1([C:7](=[C:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)[C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.CCO.[OH-].[Na+]>Cl.CCOC(C)=O>[C:1]1([C:7](=[C:21]2[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH2:26]2)[C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131728143HCID 131728143, compound

Product 1

HCID 11992477HCID 11992477, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 17 THF (35 mL) and absolute EtOH (35 mL) was charged with 1 N aqueous NaOH (46 mL) and heated to reflux. After 90 min the reaction was cooled to room temperature. The reaction was diluted with 1 N aqueous HCl (55 mL) and EtOAc (100 mL). The organic fraction iwa washed with water (2×75 mL) and brine (1000 mL) then dried (MgSO4) and concentrated to a white solid. This solid was triturated with hexane (25 mL) and recrystallized from CH3CN (100 mL) to yield: 1.87 g (84%) of the title compound 18 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.35 (s, 1H), 7.59 (d, J=8.2 Hz, 2H), 7.53 (d, J=15.9 Hz, 1H), 7.15-7.31 (m, 7H), 6.45 (d, J=15.9 Hz, 1H), 1.91 (s, 2H), 1.89 (s, 2H), 1.26 (s, 2H), 0.88 (s, 6H), 0.87 (s, 6H). LCMS (ESI): m/z 373 (M−H)−.

Workup

  1. temperatureheated to reflux
  2. washThe organic fraction iwa washed with water (2×75 mL) and brine (1000 mL)
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated to a white solid
  5. customThis solid was triturated with hexane (25 mL)
  6. customrecrystallized from CH3CN (100 mL) to yield: 1.87 g (84%) of the title compound 18 as a white solid

Sources & evidence

ORD record
ord-0418eabad2514a19bb3c42162717a675
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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