Ethyl Acetate → HCID 67469173, compound

HRID 1019758Notes

Reaction equation

HRID 1019758 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][C:14](OC)=[O:15].[Li+].[BH4-].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][OH:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 67468998HCID 67468998, compound

Product 1

HCID 67469173HCID 67469173, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 2-(2-chloro-5-methoxy-4-nitrophenyl)acetate (10.2 g, 41.86 mmol) was dissolved in dry THF (200 mL) and cooled to 0° C. A 2M solution of LiBH4 in THF (41.86 mL, 83.73 mmol) was added at 0° C. over 20 minutes then the mixture was allowed to warm to room temperature and stirred for 5 hours. Saturated NH4Cl solution was added to the reaction cautiously and stirred further for 15 minutes then EtOAc (150 mL) and water (150 mL) were added. The separated aqueous phase was extracted with EtOAc (100 mL) then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM to give the title compound (7.0 g, 72%) as a solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred further for 15 minutes
  3. extractionThe separated aqueous phase was extracted with EtOAc (100 mL)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM

Sources & evidence

ORD record
ord-58e00c8296a94496a762a8edf590a6d1
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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