Dimethylformamide → HCID 58858118, compound

HRID 1916346Notes

Reaction equation

HRID 1916346 reaction equation
[K].[N+:2]([C:5]1[CH:6]=[C:7]([OH:13])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)([O-:4])=[O:3].BrC[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH3:23]N(C=O)C>>[CH3:23][O:13][C:7]1[CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:10]=[CH:9][C:8]=1[O:11][CH2:12][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 79177tert-Butyl bromoacetateHCID 67066684HCID 67066684, compound

Product 1

HCID 58858118HCID 58858118, compoundYield 88%

Procedure

A solution of 4-nitroguaiacol potassium salt (613 mg; 2.96 mmol) and t-butyl bromoacetate (0.65 mL; 4.43 mmol) in DMF (7 mL) was stirred at rt for 0.5 h prior to dilution with H2O and extraction with EtOAc. The organic layer was washed with H2O, dried over MgSO4, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, Hexanes/EtOAc, 100:0 to 1:1 gradient) to afford the title compound (738 mg; 88%) as a beige solid. 1H NMR (CDCl3) δ 1.46 (s, 9H), 3.96 (s, 3H), 4.67 (s, 2H), 6.77 (d, J=8.79 Hz, 1H), 7.76 (d, J=2.74 Hz, 1H), 7.85 (dd, J=8.80 Hz, 2.75 Hz, 1H); 13C NMR (CDCl3) δ 27.98, 56.37, 66.18, 83.09, 107.07, 111.52, 117.28, 142.17, 149.19, 152.69, 166.66; HPLC (Method #1): 3.13 min retention time, (97%); MS (ES): m/z 306 [M+Na]+.

Workup

  1. extractionto dilution with H2O and extraction with EtOAc
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, Hexanes/EtOAc, 100:0 to 1:1 gradient)

Sources & evidence

ORD record
ord-11da3aeabfbd4f97853541288e8e7933
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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