Sodium Hydroxide → HCID 9889365, compound

HRID 650582Notes

Reaction equation

HRID 650582 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([O:30][CH2:31][CH3:32])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=3[CH:16]=2)[CH3:14])=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[CH2:31]([O:30][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=3[CH:16]=2)[CH3:14])=[CH:10][CH:11]=1)[C:3]([OH:33])=[O:2])[CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9803929HCID 9803929, compound

Product 1

HCID 9889365HCID 9889365, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-ethoxy-3-(4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphtalen-2-yl)-ethoxy)-phenyl)-propionic acid methyl ester (108 mg; 0.24 mmol) in methanol (15 ml) was treated with 1 N NaOH and the reaction mixture was stirred for 16 hours. The reaction mixture was evaporated and 0.1 N HCl (20 ml) and ethyl acetate (50 ml) was added. The organic phase was separated and the water phase was further extracted with ethyl acetate (50 ml). The combined organic phases were dried and evaporated to give crude product. Purification on column chromatography using methylene chloride:methanol (15:1) as eluent gave the title compound in 105 mg (100%) yield. Compound 3.

Workup

  1. customThe reaction mixture was evaporated
  2. addition0.1 N HCl (20 ml) and ethyl acetate (50 ml) was added
  3. customThe organic phase was separated
  4. extractionthe water phase was further extracted with ethyl acetate (50 ml)
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customto give crude product
  8. customPurification on column chromatography

Sources & evidence

ORD record
ord-6e4daf9857ad4820b3d65661e7f983be
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

Loading…