Pyridine → HCID 641127, compound

HRID 1808861Notes

Reaction equation

HRID 1808861 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[CH3:6])[CH3:2].N1C=CC=CC=1.[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16]>C(Cl)Cl>[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](=[O:16])/[C:5](/[CH3:6])=[CH:4]/[O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 5365091(1E)-1-Ethoxy-1-propene

Product 1

HCID 641127HCID 641127, compoundYield 18.64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-1-ethoxyprop-1-ene (6.41 mL, 57.9 mmol) and pyridine (4.68 mL, 57.9 mmol) was added to a soln. of 2,2,2-trichloroacetyl chloride (10.53 g, 57.9 mmol) in DCM (15 mL) at −10° C. at a rate of 6-10 drops/min. After the addition was completed, the mixture was stirred at r.t for 24 hrs. Filtered, and the filtrate was concentrated in reduced pressure (at first the temperature of the water bath was r.t, after most DCM was evaporated off, water bath was warmed to 50° C. to afford (E)-1,1,1-trichloro-4-ethoxy-3-methylbut-3-en-2-one (2.55 g, 10.79 mmol, 18.64% yield). 1H-NMR (500 MHz, CDCl3): δ: 7.96 (s, 1H), 4.21 (q, J=7.1 Hz, 2H), 1.94 (s, 3H), 1.41 (t, J=7.2 Hz, 3H). This material was taken into Step G2 without further purification.

Workup

  1. additionwas added to a soln
  2. customat −10° C.
  3. additionAfter the addition
  4. filtrationFiltered
  5. concentrationthe filtrate was concentrated in reduced pressure (at first the temperature of the water bath
  6. customafter most DCM was evaporated off

Sources & evidence

ORD record
ord-291bd1c844d447ef9b4209c6c5d1e8eb
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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