Lithium Hydroxide → HCID 9908951, compound

HRID 275969Notes

Reaction equation

HRID 275969 reaction equation
[OH-].[Li+].[CH2:3]([O:5][CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]=[C:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])[CH3:4]>C(O)C>[CH2:3]([O:5][CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]=[C:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 9823905HCID 9823905, compound

Product 1

HCID 9908951HCID 9908951, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Lithium hydroxide (1M, 1.0 ml, 1.0 mmol) was added to a suspension of ethyl 2-ethoxy-3-[4-(2-fluoren-9-ylidene-ethoxy)-phenyl]-propionate (0.214 g, 0.5 mmol) in ethanol (5 ml) and the resulting mixture heated to gentle reflux for 30 min. The cooled mixture was partitioned between water (30 ml) and dichloromethane (20 ml), acidified to pH 1 by adding 1N hydrochloric acid (3 ml), and the organic phase collected. The aqueous phase was further extracted with dichloromethane (3×20 ml) and the combined organics were washed with brine, dried (MgSO4) and evaporated to give a yellow gum. The product was purified by column chromatography on silica gel (3% methanol in dichloromethane eluent) to give 2-ethoxy-3-[4-(2-fluoren-9-ylidene-ethoxy)-phenyl]-propionic acid, as a yellow solid; 0.104 g (51%).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto gentle reflux for 30 min
  3. customThe cooled mixture was partitioned between water (30 ml) and dichloromethane (20 ml)
  4. additionby adding 1N hydrochloric acid (3 ml)
  5. customthe organic phase collected
  6. extractionThe aqueous phase was further extracted with dichloromethane (3×20 ml)
  7. washthe combined organics were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a yellow gum
  11. customThe product was purified by column chromatography on silica gel (3% methanol in dichloromethane eluent)

Sources & evidence

ORD record
ord-d84edb0a33ed4b9ca063fa142a2854db
Source dataset
uspto-grants-2002_03
Patent number
US06353018B1

Reaction notes

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