Water → HCID 18174716, compound

HRID 395667Notes

Reaction equation

HRID 395667 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[O:16][C:15]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[N:14][C:13]=2[CH2:23][CH2:24][CH2:25][C:26](OCC)=[O:27])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[O:16][C:15]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[N:14][C:13]=2[CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18174732HCID 18174732, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18174716HCID 18174716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(4-fluoro-1-naphthyl)-2-(2-methyl-1-imidazolyl)-4-oxazolebutanoate (401 mg) was dissolved in 10 ml of tetrahydrofuran, to which was added gradually lithium aluminum hydride (50 mg) under ice-cooling, and the mixture was stirred for 1 hour. Water (0.1 ml) was carefully added to the reaction mixture, which was filtered. The residue on the filter paper was washed with ethyl acetate. The filtrate was concentrated to give crystals of 5-(4-fluoro-1-naphthyl)-2-(2-methyl-1-imidazolyl)-4-oxazolebutanol. Recrystallization from acetone-diethyl ether gave colorless prisms (294 mg, 82%). Melting point 107-109° C.

Workup

  1. temperaturecooling
  2. filtrationwas filtered
  3. washThe residue on the filter paper was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ca3436c740b24956bc5a081742452d80
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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