Tetrahydrofuran → HCID 68308536, compound

HRID 1021232Notes

Reaction equation

HRID 1021232 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C.C1COCC1.[BH4-].[Li+].[Cl-].[NH4+]>CCOC(C)=O>[OH:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 86686209HCID 86686209, compound

Product 1

HCID 68308536HCID 68308536, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(2-ethoxy-2-oxoethyl)benzoate (1.41 g) was mixed with THF (20 ml), and lithium borohydride (260 mg) was added thereto at 0° C., followed by stirring at room temperature overnight. A saturated ammonium chloride solution and EtOAc were added to the reaction mixture at 0° C. The organic layer was washed with water and saturated brine, dried over Na2SO4, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain ethyl 3-(2-hydroxyethyl)benzoate (824 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-9510761e7e6044fb9aacf341f985ec01
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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