Water → [2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]methanol

HRID 350736Notes

Reaction equation

HRID 350736 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:17](OC)=[O:18])=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:1][C:2]1[O:3][C:4]([CH2:17][OH:18])=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23061895Methyl [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylate

Product 1

HCID 23061954[2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]methanolYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylate (4.5 g) in diethyl ether (90 mL) was added lithium aluminum hydride (0.63 g) at 0° C. After stirring the reaction mixture at room temperature for 30 min, water (3.2 mL) was added, and the precipitated solid was removed by filtration. The filtrate was concentrated and the obtained solid was washed with isopropyl ether to give [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]methanol (3.63 g, yield 90%) as crystals. Recrystallization from ethanol gave colorless crystals. melting point: 132–133° C.

Workup

  1. customthe precipitated solid was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. washthe obtained solid was washed with isopropyl ether

Sources & evidence

ORD record
ord-06439c5e689a4a0a9c4edb587e2f9dca
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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