Methanol → HCID 66878002, compound

HRID 220299Notes

Reaction equation

HRID 220299 reaction equation
C([O:5][C:6](=[O:23])[CH2:7][C:8]1([OH:22])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C.O[Li].O.O.CO>CCO>[OH:22][C:8]1([CH2:7][C:6]([OH:23])=[O:5])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 77200910HCID 77200910, compound

Product 1

HCID 66878002HCID 66878002, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.0 g of rac-(1R*,2R*,4R*)-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid tert.-butyl ester dissolved in 25 mL EtOH were added 2.1 g of LiOH.H2O, 8 mL H2O and 22 mL MeOH. The reaction mixture was stirred at rt for 3 days and then concentrated. The residue was partitioned between water and Et2O. The aq. layer was separated and acidified with 1N HCl resulting in the formation of a white solid. The solid was filtrated, washed with 5 mL dil. HCl and dried in vacuo to obtain 3.19 g of rac-(1R*,2R*,4R*)-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid as white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water and Et2O
  3. customThe aq. layer was separated
  4. filtrationThe solid was filtrated
  5. washwashed with 5 mL dil. HCl
  6. customdried in vacuo

Sources & evidence

ORD record
ord-22f9fe3a589443adbc5325eb1c9c8562
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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