Triethylamine → HCID 86702739, compound

HRID 511750Notes

Reaction equation

HRID 511750 reaction equation
[CH3:1][O:2][N:3]=[CH:4][CH:5]1[CH2:12][CH:11]2[CH:7]([C:8]([OH:25])=[C:9]([C:14]3[C:19]([CH2:20][CH3:21])=[CH:18][C:17]([CH3:22])=[CH:16][C:15]=3[CH2:23][CH3:24])[C:10]2=[O:13])[CH2:6]1.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>ClCCl>[CH3:28][C:27]([CH3:30])([CH3:29])[C:26]([O:13][C:10]1[CH:11]2[CH:7]([CH2:6][CH:5]([CH:4]=[N:3][O:2][CH3:1])[CH2:12]2)[C:8](=[O:25])[C:9]=1[C:14]1[C:15]([CH2:23][CH3:24])=[CH:16][C:17]([CH3:22])=[CH:18][C:19]=1[CH2:20][CH3:21])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86702740HCID 86702740, compound

Product 1

HCID 86702739HCID 86702739, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.104 g (0.31 mmol) of 5-(2,6-diethyl-4-methylphenyl)-6-hydroxy-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehyde O-methyloxime (compound I-a-13 according to the invention), 0.040 g (0.34 mmol) of pivaloyl chloride and 92 mg (0.91 mmol) of triethylamine in 8 ml of dichloromethane are stirred at room temperature for 2 h. The mixture is poured onto ice, taken up in dichloromethane, washed with water, dried (magnesium sulphate) and concentrated using a rotary evaporator. Chromatography on silica gel (mobile phase ethyl acetate/hexane v:v=25:75) gives 107 mg of the title compound as a colourless oil.

Workup

  1. additionThe mixture is poured onto ice
  2. washwashed with water
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-e5d3c58fcf484f47abf24bfa88344faa
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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