Ethanol → HCID 11992565, compound

HRID 2241039Notes

Reaction equation

HRID 2241039 reaction equation
[C:1]1([C:7](=[C:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[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:18]2[CH2:19][C:20]([CH3:27])([CH3:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH2:23]2)[C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68502575HCID 68502575, compound

Product 1

HCID 11992565HCID 11992565, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20, THF (15 mL), EtOH (15 mL) is charged with 1 N aqueous NaOH (20 mL) and heated to reflux. After 4 h the reaction was allowed to cool to room temperature and then diluted with 1 N aqueous HCl (30 mL) and EtOAc (50 mL). The organic fraction was washed with water (2×40 mL) and brine (40 mL) then dried (Na2SO4). After concentrating, the solid was triturated with hexane (25 mL), filtered and air-dried to afford 770 mg (86%) of the title compound 21 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.82 (s, 1H), 7.86 (d, J=8.2 Hz, 2H), 7.16-7.29 (m, 7H), 1.90 (s, 2H), 1.88 (s, 2H), 1.26 (s, 2H), 0.88 (s, 12H). LCMS (ESI): m/z 347 (M−H)−. Anal. Calcd for C24H28O2: C, 82.69; H, 8.12. Found: C, 82.48; H, 8.14.

Workup

  1. temperatureheated to reflux
  2. washThe organic fraction was washed with water (2×40 mL) and brine (40 mL)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationAfter concentrating
  5. customthe solid was triturated with hexane (25 mL)
  6. filtrationfiltered
  7. customair-dried

Sources & evidence

ORD record
ord-0002f7cd734e4f638d93d54b213f6e12
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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