Water → HCID 86755321, compound

HRID 1004330Notes

Reaction equation

HRID 1004330 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][CH:12]([C:20](=[O:22])[CH3:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1)=[O:5])[CH3:2].O>O1CCCC1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][CH:12]([CH:20]([OH:22])[CH3:21])[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 18794887HCID 18794887, compound

Product 1

HCID 86755321HCID 86755321, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 3611392Lithium tri-s-butylborohydrideSolvent

Procedure

To 2.26 g of tert-butyl 2-{5-(ethoxycarbonyl)-2-furylmethyl}-3-oxobutanoate in 50 ml of tetrahydrofuran, 7.7 ml of 1M lithium tri-sec-butylborohydride in tetrahydrofuran solution was added at -78° C. under stirring, and the resulting reaction solution was stirred at the same temperature for 2 hours. After addition of water, the reaction solution was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=12/1→4/1] to give 1.65 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. stirringwas stirred at the same temperature for 2 hours
  3. stirringthe reaction solution was stirred at room temperature for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=12/1→4/1]

Sources & evidence

ORD record
ord-6b27b8236fb34940a2cb334dfc39720c
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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