Tetrahydrofuran → HCID 70099111, compound

HRID 2300667Notes

Reaction equation

HRID 2300667 reaction equation
[BH4-].[Na+].O1CCCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])[O:18][C:19]=2[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:10]=1>CC(O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]=[C:17]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])[O:18][C:19]=2[CH:20]([OH:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 54455876HCID 54455876, compound

Product 1

HCID 70099111HCID 70099111, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium borohydride(95 mg) was added to a tetrahydrofuran(60 ml)-2-propanol(30 ml) solution of ethyl 2-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]-2-oxoacetate(2.93 g) at 0° C. After stirring for 30 minutes, the reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated to give ethyl 2-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]-2-hydroxyacetate(2.20 g, 75%). This was recrystallized from acetone-ethyl acetate to give colorless prisms. mp 197-198° C. (degradation)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-43384b5b9e644df59483df12c6ed74fb
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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