Lithium hydroxide, monohydrate → Tert-butyl 6-(4-carboxyphenyl)-spiro[2.5]octane-1-carboxylate

HRID 1035705Notes

Reaction equation

HRID 1035705 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:26][CH2:25][C:15]3([CH:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5])C.C1COCC1.CO.O.[OH-].[Li+]>O>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:26][CH2:25][C:15]3([CH:17]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 66740128HCID 66740128, compound

Product 1

HCID 66739947Tert-butyl 6-(4-carboxyphenyl)-spiro[2.5]octane-1-carboxylateYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.159 g of tert-butyl 6-(4-ethoxycarbonylphenyl)spiro[2.5]octane-1-carboxylate (0.44 mmol, 1 eq.) is placed in 4 mL of a 3/1 mixture of THF/methanol in a 50 mL round-bottomed flask. 0.075 g of lithium hydroxide monohydrate (1.78 mmol; 4 eq.) dissolved in 1 mL of water is added with stirring. After 16 hours at room temperature, the reaction medium is evaporated and aqueous 6% sulfur dioxide solution is added. The precipitate is filtered off to give 0.122 g of tert-butyl 6-(4-carboxyphenyl)-spiro[2.5]octane-1-carboxylate.

Workup

  1. additionis added
  2. customthe reaction medium is evaporated
  3. additionaqueous 6% sulfur dioxide solution is added
  4. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-a7235f46bc6b49ce94ea4ba5ff1c3272
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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