Sodium sulfate decahydrate → 3-Ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 1295215Notes

Reaction equation

HRID 1295215 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])[CH:8]=[C:7]([O:25][CH2:26][CH3:27])[CH:6]=1)C.[H-].[Li+].[Al+3].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:26]([O:25][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:16][C:17]=2[CH3:18])[CH:8]=1)[CH2:4][OH:3])[CH3:27]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 22930682Ethyl 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzoate

Product 1

HCID 694273333-Ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcoholYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzoate (5.40 g) in tetrahydrofuran (80 ml) was gradually added aluminum lithium hydride (540 mg) at 0° C. and the mixture was stirred for 1 hr. Sodium sulfate 10 hydrate (4.60 g) was added to the reaction mixture and the mixture was further stirred for 30 min. The insoluble materials were filtered off, and the filtrate was concentrated. The obtained crystals were recrystallized from ethyl acetate-isopropyl ether to give 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (4.44 g, 92%) as colorless needle-shaped crystals. melting point: 103–104° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was further stirred for 30 min
  3. filtrationThe insoluble materials were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe obtained crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-b2c65d1d1220496bb4a50abd327355f0
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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