Ethyl Acetate → 2-(4-Amino-2-chlorophenoxy)ethan-1-ol

HRID 633444Notes

Reaction equation

HRID 633444 reaction equation
C([Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=1[Cl:21])(C)C)(C)(C)C.O.O.Cl[Sn]Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>CCO>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[C:13]([Cl:21])[CH:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 86704535Tert-butyl-(2-(2-chloro-4-nitrophenoxy)ethoxy)dimethylsilane

Product 1

HCID 196227612-(4-Amino-2-chlorophenoxy)ethan-1-olYield 3.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl-(2-(2-chloro-4-nitrophenoxy)ethoxy)dimethylsilane (475 mg, 1.4 mmol) and SnCl2.2H2O (1.07 g, 5.7 mmol) in EtOH (40 mL) was heated to reflux and stirred for 4 hr. After allowing to cool, the mixture was poured into EtOAc (50 mL) and saturated NaHCO3 (50 mL), then filtered through celite. The filtrate was partitioned and the aqueous layer extracted with EtOAc (2×50 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was dry-loaded on to silica gel and purified by column chromatography on silica gel using EtOAc/heptane (2:8 to 1:0) as eluent to give the product (9 mg, 3% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationfiltered through celite
  5. customThe filtrate was partitioned
  6. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto leave a crude residue
  11. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-59aa6dec782d493294b5142e45056e38
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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