Ethanol → HCID 42602682, compound

HRID 2070567Notes

Reaction equation

HRID 2070567 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]2[CH2:18][CH2:17][C:16]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15]2)=[CH:8][CH:7]=1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH2:15]1[C:16]2([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:17][CH2:18][CH:14]1[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57771464HCID 57771464, compound

Product 1

HCID 42602682HCID 42602682, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(spiro[4.6]undec-2-ylmethoxy)-phenyl]-propionic acid methyl ester (75 mg) obtained in Step 8 in a mixed solvent of ethanol (1 mL)-tetrahydrofuran (1 mL) was added 1N aqueous sodium hydroxide solution (0.22 mL), followed by stirring the reaction mixture at room temperature for 5 hours. Then, after concentrating the reaction mixture, to the residue was added dropwise 2N aqueous hydrochloric acid solution. The precipitate was filtered, washed with water and dried in vacuo to give 3-[4-(spiro[4.6]undec-2-ylmethoxy)-phenyl]-propionic acid (70.6 mg) as the desired compound.

Workup

  1. concentrationThen, after concentrating the reaction mixture
  2. additionto the residue was added dropwise 2N aqueous hydrochloric acid solution
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f3cdb71052d041c9a441521f52fa8a21
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

Loading…