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Hydrochloric Acid → 8-(2-Hydroxymethyl-4,5,6,7-tetramethoxyindan-2-yl)octanol

HRID 2268448
Notes
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Reaction equation

HRID 2268448 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](OCC)=[O:37])[CH2:20][C:19]2[C:14](=[C:15]([O:27][CH3:28])[C:16]([O:25][CH3:26])=[C:17]([O:23][CH3:24])[C:18]=2[O:21][CH3:22])[CH2:13]1)=O)C.Cl>C(OCC)C>[OH:9][CH2:10][C:12]1([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[CH2:13][C:14]2[C:19](=[C:18]([O:21][CH3:22])[C:17]([O:23][CH3:24])=[C:16]([O:25][CH3:26])[C:15]=2[O:27][CH3:28])[CH2:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 183485878-(2-Hydroxymethyl-4,5,6,7-tetramethoxyindan-2-yl)octanolYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl Ether
Solvent

Procedure

Lithium aluminium hydride (72.1 mg, 1.90 mmols) was added to a diethyl ether (6.0 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (315 mg, 0.634 mmols), with cooling with ice. The reaction mixture was warmed to room temperature, and then stirred for 1 hour. 1N hydrochloric acid was added to the reaction mixture with cooling with ice, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1) to obtain the entitled compound (239 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice, which
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. customThe solvent was evaporated out
  7. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-5955a4ef64064b4f868fc5aa35f28134
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes