Sodium Hydroxide → HCID 69880872, compound

HRID 1841282Notes

Reaction equation

HRID 1841282 reaction equation
[OH-].[Na+].[CH:3]1[C:13]2[C:12](=[CH:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=3)[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:3]1[C:13]2[C:12](=[CH:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69882181HCID 69882181, compound

Product 1

HCID 69880872HCID 69880872, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1M, 2.5 ml, 2.5 mmol) was added to a solution of a 4:1 E/Z double-bond isomer mixture of ethyl 3-{4-[3-(6H-dibenzo[b,e]oxepin-11-ylidene)-propoxy]-phenyl}-2-ethoxy-propionate (0.24 g, 0.51 mmol) in ethanol (5 ml) and the mixture stirred at room temperature for 78 h. The resulting mixture was partitioned between 1N hydrochloric acid (20 ml) and dichloromethane (20 ml), and the organic phase collected. The aqueous phase was further extracted with dichloromethane (3×20 ml) and the combined organics washed with brine, dried (Na2SO4) and evaporated to give a pale yellow gum. This was then purified by column chromatography on silica gel (3% methanol in dichloromethane eluent) to give the title compound as an inseparable 4:1 mixture of E and Z double-bond isomers, as a pale yellow glass; 0.186 g (80%).

Workup

  1. customThe resulting mixture was partitioned between 1N hydrochloric acid (20 ml) and dichloromethane (20 ml)
  2. customthe organic phase collected
  3. extractionThe aqueous phase was further extracted with dichloromethane (3×20 ml)
  4. washthe combined organics washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give a pale yellow gum
  8. customThis was then purified by column chromatography on silica gel (3% methanol in dichloromethane eluent)

Sources & evidence

ORD record
ord-5e0ab55a7da1459aa454df7a5038c542
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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