Triethylamine → HCID 21883645, compound

HRID 722286Notes

Reaction equation

HRID 722286 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([Cl:11])[CH:7]=[C:4]([CH:5]=O)[C:3]=1[OH:12].[F:13][C:14]([F:23])([F:22])/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[Cl:11][C:8]1[C:9]([CH3:10])=[C:2]([Cl:1])[C:3]2[O:12][CH:15]([C:14]([F:13])([F:23])[F:22])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][C:4]=2[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoateHCID 21883589HCID 21883589, compound

Product 1

HCID 21883645HCID 21883645, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3,5-dichloro-4-methylsalicylaldehyde (Step 1)(5.94 g, 29.0 mmol) and ethyl 4,4,4-trifluorocrotonate (7.67 g, 45.6 mmol) dissolved in anhydrous DMSO (10 mL) was treated with triethylamine (5.88 g, 58.1 mmol). The reaction was stirred at 85° C. for 49 hours then cooled in ice and filtered to give an orange solid. The solid was dissolved in ethyl acetate (100 mL), washed with 3 N HCl (2×50 mL), saturated NaHCO3, washed with brine, dried over MgSO4, and concentrated in vacuo to give a yellow solid (8.63 g, 84%): mp 117.1–119.5° C. 1H NMR (CDCl3/300 MHz) 7.63 (s, 1H), 7.17 (s, 1H), 5.80 (q, 1H, J=6.6 Hz), 4.33 (m, 2H), 2.48 (s, 3H), 1.35 (t, 3H, J=7.1 Hz).

Workup

  1. temperaturethen cooled in ice
  2. filtrationfiltered
  3. customto give an orange solid
  4. washwashed with 3 N HCl (2×50 mL), saturated NaHCO3
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b98aff75af2941adb541898f7d5bdd16
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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