Sodium Hydroxide → 8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

HRID 2268445Notes

Reaction equation

HRID 2268445 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate

Product 1

HCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acidYield 22.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprised of an ethanol (8 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (367 mg, 0.764 mmols) and an aqueous sodium hydroxide solution (1N, 0.764 ml, 0.764 mmols) was stirred at room temperature for 6 hours, and an aqueous sodium hydroxide solution (1 N, 0.153 ml, 0.153 mmols) was added thereto and the stirring was continued at room temperature for further 6 hours. The reaction mixture was concentrated in vacuo, which was made acidic by adding 1 N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2) to obtain the entitled compound (78.6 mg) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, which
  2. additionby adding 1 N hydrochloric acid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2)

Sources & evidence

ORD record
ord-1636f8a4bf514b4fb53f0e19e61a2d2b
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…