Water → HCID 4983340, compound

HRID 650578Notes

Reaction equation

HRID 650578 reaction equation
[CH3:1][C:2]1[C:3]([C:16](=[O:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.CCOCC>C1COCC1>[CH3:1][C:2]1[C:3]([CH:16]([OH:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 4983340HCID 4983340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (500 mg; 2.0 mmol) in dry THF (5 ml) was added slowly LiAlH4 (80 mg; 2.0 mmol) at 0° C. The reaction mixture was stirred for 3 hours, and then water (20 ml) was added. Ether (50 ml) was added and the mixture was filtered through filter aid. The organic phase was separated and the water phase was extracted with ether. The combined organic phases were dried and evaporated to give the title compound in 504 mg (100%) yield.

Workup

  1. filtrationthe mixture was filtered
  2. filtrationthrough filter aid
  3. customThe organic phase was separated
  4. extractionthe water phase was extracted with ether
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-766998d0223d4c08bf3c39ad50323c89
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

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