Hydrochloric Acid → HCID 18348590, compound

HRID 2268452Notes

Reaction equation

HRID 2268452 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[C:15]([O:22][CH3:23])=[C:14]2[C:10]=1[CH2:11][CH:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](OCC)=[O:32])[CH2:13]2.Cl>C(OCC)C>[CH3:23][O:22][C:15]1[C:16]([O:20][CH3:21])=[C:17]([O:18][CH3:19])[C:9]([O:8][CH3:7])=[C:10]2[C:14]=1[CH2:13][CH:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18348610HCID 18348610, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18348590HCID 18348590, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (41.8 mg, 1.10 mmols) was added to a diethyl ether (3.0 ml) solution of ethyl 8-(4,5,6,7-tetramethoxyindan-2-yl)octanoate (150 mg, 367 mmols), with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. 1 N hydrochloric acid was added to the reaction mixture, which 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=10:1 to 4:1) to obtain the entitled compound (138 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas 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=10:1 to 4:1)

Sources & evidence

ORD record
ord-036f84de7fcd4ca0a1a2f35a76917a3c
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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