Ethyl Acetate → (2-(2-(2-(4-Butyrylphenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

HRID 2406594Notes

Reaction equation

HRID 2406594 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].I[CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[CH:34][CH:33]=1.C(OCC)(=O)C>CN(C=O)C>[C:38]([C:35]1[CH:36]=[CH:37][C:32]([O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[CH:33][CH:34]=1)(=[O:42])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 279800Di-tert-butyl IminodicarboxylateHCID 23665647Potassium tert-butoxideHCID 66822250HCID 66822250, compound

Product 1

HCID 68041436(2-(2-(2-(4-Butyrylphenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Di-tert-butyliminodicarboxylate (3.05 g, 14.07 mmol) and potassium tert-butoxide (1.58 g, 14.07 mmol) were stirred in DMF (50 mL) for 15 minutes followed by the addition of 1-(4-(2-(2-(2-iodoethoxy)ethoxy)ethoxy)phenyl)butan-1-one (43; 3.81 g, 9.38 mmol). The resulting mixture was stirred under nitrogen for 18 hours, and then poured into 200 mL of ethyl acetate. This solution was washed with water (2×) and sat. brine, dried over sodium sulfate, and concentrated to afford a liquid that was purified by flash silica gel column chromatography, eluting with 3:1 hexanes/ethyl acetate to afford 44 (2.27 g, 49%) as a clear oil: MS (ES+) m/z 496.2 (M+H)+.

Workup

  1. washThis solution was washed with water (2×) and sat. brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford a liquid that
  5. customwas purified by flash silica gel column chromatography
  6. washeluting with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d29cfd50b01f4d8181a8d70381842ac6
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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