Triethylamine → HCID 70980420, compound

HRID 1409362Notes

Reaction equation

HRID 1409362 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[CH3:10][CH:11]([CH3:16])[CH:12]([OH:15])[C:13]#[CH:14].CCN(CC)CC>C1(C)C=CC=CC=1.CCOC(C)=O>[OH:15][CH:12]([C:13]1[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:14]=1)[CH:11]([CH3:16])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 982794-Methylpentyn-3-olHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 70980420HCID 70980420, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl chlorooximidoacetate (6.79 mmol, 1.029 g) and 4-methyl-1-pentyn-3-ol (20.38 mmol, 2 g) were dissolved in toluene (20 ml). Et3N (6.79 mmol, 0.947 ml) dissolved in toluene was added dropwise. The mixture was stirred overnight at RT. The mixture was diluted with EtOAc and washed with water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.828 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 0.92 (d, 3H), 0.97 (d, 3H), 1.39 (t, 3H), 2.03-2.16 (m, 1H), 4.41 (q, 2H), 4.58 (d, 1H), 6.65 (s, 1H).

Workup

  1. additionwas added dropwise
  2. washwashed with water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-328d2229dd95427db96faa4169a34565
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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