Ethanol → HCID 131735471, compound

HRID 633579Notes

Reaction equation

HRID 633579 reaction equation
[CH2:1]([O-])C.[Na+].C(O)C.[Br:8][C:9]1[C:14]([N+]([O-])=O)=[CH:13][CH:12]=[CH:11][C:10]=1[O:18][CH2:19][CH:20]1[CH2:22][CH2:21]1.[N:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N+:24]=[N-:25]>>[N:23](/[C:26](=[CH:1]\[C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([O:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)[C:9]=1[Br:8])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N+:24]=[N-:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 90416340HCID 90416340, compound

Product 1

HCID 131735471HCID 131735471, compoundYield 28%

Conditions

Temperature
-20 °C

Procedure

A 50 mL roundbottom flask with stirbar was charged with sodium ethanolate, 21 wt % in ethanol (14 mL, 37.6 mmol), sealed and cooled to −20° C. under nitrogen. A mixture of Example 99A (6.38 g, 25.01 mmol) and ethyl 2-azidoacetate (10 g, 77 mmol) were added dropwise over 15 minutes. The solution was stirred for 3.5 hours, then poured into a separatory funnel and extracted from 100 mL water with 3×100 mL ether. The combined organics were washed with saturated aqueous sodium chloride, dried over magnesium sulfate. After filtration and solvent removal the residues were chromatographed on a 60 g silica cartridge eluting with 0-10-100% ethyl acetate/heptane to provide 2.56 g (28%) of the title compound.

Workup

  1. customsealed
  2. additionpoured into a separatory funnel
  3. extractionextracted from 100 mL water with 3×100 mL ether
  4. washThe combined organics were washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration and solvent removal the residues
  7. customwere chromatographed on a 60 g silica cartridge
  8. washeluting with 0-10-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-0547922a5ff948fd8e5e8e3e4cd466bd
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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