Sodium sulfate decahydrate → HCID 18174753, compound

HRID 563085Notes

Reaction equation

HRID 563085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25](OC)=[O:26])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][CH2:25][OH:26])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 18174760HCID 18174760, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18174753HCID 18174753, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-[2-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propoxy]phenyl]propionate (400 mg) and tetrahydrofuran (10 ml) was added gradually lithium aluminum hydride (40 mg) under ice-cooling, and the resulting mixture was stirred for 1 hour. Sodium sulfate decahydrate (400 mg) 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, and hexane was added to the residue to give crystals of 4-(4-chlorophenyl)-5-[3-(2-(3-hydroxypropyl)phenoxy)propyl]-2-(2-methyl-1-imidazolyl)oxazole (264 mg, 65%). Recrystallization from ethyl acetate-hexane gave colorless prisms. Melting point 119-120° C.

Workup

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

Sources & evidence

ORD record
ord-51ca6374e82240989be412f640bf7d07
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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