Water → 7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1790491Notes

Reaction equation

HRID 1790491 reaction equation
FC1C=CC(CC(N2CCN([CH:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=4)[CH2:20][CH2:19][CH2:18]3)CC2)=O)=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:35].[OH-].[Na+]>C1COCC1>[OH:35][CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=2)[CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 220381781-[4-(4-Fluorophenylacetyl)piperazin-1-yl]-7-methoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 122431977-Methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(4-Fluorophenylacetyl)piperazin-1-yl]-7-methoxy-1,2,3,4-tetrahydronaphthalene (0.41 g) and lithium aluminum hydride (0.05 g) were heated under reflux in THF (15 ml) for 6 hr. Next, the reaction solution was cooled and water (50 ml) a 5 N aqueous solution (50 ml) of sodium hydroxide and further water (150 ml) were successively added thereto. After stirring the resultant mixture at room temperature for 1 hr, the resulting precipitate was filtered through celite and washed with THF. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (toluene/acetone system) to give the title compound (0.38 g) as an oil.

Workup

  1. temperatureNext, the reaction solution was cooled
  2. filtrationthe resulting precipitate was filtered through celite
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-efa657249b23494891be2e7eafdbf131
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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