Sodium ethoxide → HCID 67099826, compound

HRID 1868950Notes

Reaction equation

HRID 1868950 reaction equation
[Cl:1][C:2]1[C:3](/[C:19](/[OH:26])=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]([C:8]2([C:14](OCC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CC[O-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:19]([OH:26])[CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14](=[O:15])[C:8]12[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86629263HCID 86629263, compound

Product 1

HCID 67099826HCID 67099826, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-ethyl 4-(3-chloro-2-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (0.14 g, 0.37 mmol) in 5 mL EtOH was treated with NaOEt (from 0.1 g Na reacted with 5 mL EtOH). The mixture was stirred at room temperature for 2 hours, quenched with 20 mL water, and neutralized with 5N HCl to pH=5. The mixture was extracted with EtOAc 3×50 mL. The combined organic layers were washed with saturated NaCl (20 mL), dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by column chromatography (10-40% EtOAc/hexane) to give 67 mg white solid. MS m/e: (M+H)+ 337.

Workup

  1. customquenched with 20 mL water
  2. extractionThe mixture was extracted with EtOAc 3×50 mL
  3. washThe combined organic layers were washed with saturated NaCl (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography (10-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-74df6924e65d4f25a99b49e3c67463c5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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