HCID 66756606, compound → HCID 66757012, compound

HRID 1642630Notes

Reaction equation

HRID 1642630 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=1)C(OC(C)(C)C)=O)[CH3:2]>C(O)=O>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=1)[CH3:2]

Participants

3

Reactant 1

HCID 66756606HCID 66756606, compound

Product 1

HCID 66757012HCID 66757012, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-(3-Benzyloxy-4-nitrophenyl)-malonic acid tert-butyl ester ethyl ester (5.00 g, 12.0 mmol) is suspended in formic acid (60 mL) and stirred at RT for 18 h. The solvent is removed under reduced pressure and the residue taken up in EtOAc (100 mL). The organic solution is extracted with saturated NaHCO3 (2×50 mL) and brine (30 mL), before being dried over Na2SO4 and concentrated to an oil. Purification by flash column (10-15% EtOAc/hexanes) affords (3-benzyloxy-4-nitrophenyl)-acetic acid ethyl ester as a yellow oil: MS (M+H)+=316.

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionThe organic solution is extracted with saturated NaHCO3 (2×50 mL) and brine (30 mL)
  3. dry with materialbefore being dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customPurification by flash column (10-15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-23d49581e8ab4173bcc0c0733c756f0c
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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