Sodium Hydroxide → 5-(Benzyloxy)-2-(hydroxymethyl)-3,4-dihydronaphthalene

HRID 1271268Notes

Reaction equation

HRID 1271268 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([C:19](OC)=[O:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([CH2:19][OH:20])=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 229320125-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene

Product 1

HCID 229320215-(Benzyloxy)-2-(hydroxymethyl)-3,4-dihydronaphthaleneYield 89.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21225700DiisobutylaluminumhydrideSolvent

Procedure

Under an argon atmosphere, to a solution of 2.79 g of 5-(benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene in 30 ml of dry dichloromethane, 24 ml of diisobutylaluminum hydride (1M toluene solution) was added dropwise at −70° C. or lower, followed by stirring for 20 minutes. To the reaction solution, 26 ml of an aqueous 10% sodium hydroxide solution was added dropwise and, after heating to room temperature, the mixture was extracted with diethyl ether. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.25 g of the desired compound as a colorless crystal having a melting point of 59 to 61° C.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-058514802e3b4bd8aa1af909efe752e8
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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