Diisobutylaluminum hydride → 2-(4'-Methoxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 36741Notes

Reaction equation

HRID 36741 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])=[CH:14][CH:13]=1>C1COCC1>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]2[OH:28])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 107771991(2H)-NAPHTHALENONE, 3,4-DIHYDRO-2-(4-METHOXYPHENYL)-

Product 1

HCID 106109652-(4'-Methoxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-olYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Step A Add DIBAL-H (83.8 mL, 83.8 mmol, 1M in THF) dropwise to a -78° C. solution of 2-(4'-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-1-one (7.15 g, 27.94 mmol) in anhydrous THF (150 mL). Allow the reaction to come to room temperature overnight. Cool the mixture to 0° C. and quench with sodium sulfate decahydrate. Stir the mixture overnight, then vacuum filter and thoroughly wash the filtercake with THF. Concentrate the filtrate in vacuo, then chromatograph the resulting oil on silica gel using 20% EtOAc/hexanes to give a solid. Recrystallize from EtOAc/hexane to obtain 4.84 g (67%) of 2-(4'-methoxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-ol, mp 89°-90.5° C.

Workup

  1. customdropwise to a -78° C.
  2. customthe reaction
  3. customquench with sodium sulfate decahydrate
  4. filtrationvacuum filter
  5. washthoroughly wash the filtercake with THF
  6. concentrationConcentrate the filtrate in vacuo
  7. customchromatograph the resulting oil on silica gel using 20% EtOAc/hexanes to give a solid
  8. customRecrystallize from EtOAc/hexane

Sources & evidence

ORD record
ord-c47b0b74410b44e59148c66ec887df03
Source dataset
uspto-grants-1995_05
Patent number
US05416118

Reaction notes

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