Triethylamine → HCID 67168642, compound

HRID 872893Notes

Reaction equation

HRID 872893 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[CH3:10][CH:11]([OH:15])[CH2:12][C:13]#[CH:14].C(N(CC)CC)C>C(OCC)C>[OH:15][CH:11]([CH3:10])[CH2:12][C:13]1[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 929154-Pentyn-2-olHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 67168642HCID 67168642, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl chlorooximidoacetate (4 g, 26.4 mmol) and 4-pentyn-2-ol (10.00 ml, 107 mmol) were dissolved in diethyl ether (30 ml). A solution of triethylamine (3.68 ml, 26.4 mmol) in diethylether (20 ml) was added dropwise to the reaction mixture. After 1 h of stirring at RT the reaction mixture was washed with brine and water, dried with MgSO4 and evaporated to dryness. The residue was purified with flash chromatography using a gradient of methanol in methylene chloride affording 2.51 g (48%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ, 1.11 (d, 3H), 1.31 (t, 3H), 2.82-2.94 (m, 2H), 3.93-4.03 (m, 1H) 4.35 (q, 2H), 4.89 (d, 1H), 6.67 (s, 1H).

Workup

  1. washwas washed with brine and water
  2. dry with materialdried with MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-1b8d3b9e80c247799ac462e93de06472
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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