Hydrochloric Acid → Ethyl 2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

HRID 2268447Notes

Reaction equation

HRID 2268447 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)=[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].Cl>C1COCC1>[OH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

Product 1

HCID 18348653Ethyl 2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylateYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of borane complex (1 M, 3.74 ml, 3.74 mmols) was added to a THF (9.0 ml) solution of 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (847 mg, 1.87 mmol), with cooling with ice. The reaction mixture was allowed to warm to room temperature, and then stirred for 2 hours. 1N hydrochloric acid was added and the reaction mixture was then extracted 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=4:1) to obtain the entitled compound (713 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionthe reaction mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried
  5. customThe solvent was evaporated out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dd8bc324383d4b098efc971fd0b57eaa
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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