Lithium Hydroxide → HCID 58575303, compound

HRID 1189461Notes

Reaction equation

HRID 1189461 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([O:16]CC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58575621HCID 58575621, compound

Product 1

HCID 58575303HCID 58575303, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5.18 g of ethyl cis-2-benzyloxy-1-cyclopentane carboxylate and 120 mL of tetrahydrofuran was added 63.0 mL of a 1 M aqueous lithium hydroxide solution, followed by stirring at room temperature for 2 days. The reaction liquid was concentrated under reduced pressure, and then to the residue were added water and 1 M hydrochloric acid to adjust the pH to about 2, followed by stirring at room temperature for 1 hour. The precipitated solid was collected by filtration and dried under reduced pressure. The obtained crude product was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 3.73 g of cis-2-benzyloxy-1-cyclopentanecarboxylic acid as a pale yellow solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionto the residue were added water and 1 M hydrochloric acid
  4. stirringby stirring at room temperature for 1 hour
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a128196e42e44d3fb3c497832e1f46a4
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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