Triethylamine → HCID 88657308, compound

HRID 2309229Notes

Reaction equation

HRID 2309229 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([CH:14]([C:16]([F:19])([F:18])[F:17])[OH:15])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]([Cl:31])=[CH:22][C@@H:23]1[C@H:25]([C:26](Cl)=[O:27])[C:24]1([CH3:30])[CH3:29].C(N(CC)CC)C>O1CCCC1>[O:1]([C:8]1[N:13]=[C:12]([CH:14]([O:15][C:26]([C@H:25]2[C@@H:23]([CH:22]=[C:21]([Cl:20])[Cl:31])[C:24]2([CH3:30])[CH3:29])=[O:27])[C:16]([F:19])([F:17])[F:18])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideHCID 15592688HCID 15592688, compound

Product 1

HCID 88657308HCID 88657308, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.04 g (7.6 mmol) of the 6-phenoxy-α-(trifluoromethyl)-2-pyridinemethanol of Step C and 1.72 g (7.6 mmol) of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride in 30 ml of dry tetrahydrofuran was added 2.0 ml (14.2 mmol) of triethylamine. The reaction was stirred for 72 hours. The precipitated triethylamine hydrochloride was then filtered off and the filtrate was concentrated under vacuum. The residue was chromatographed through silica gel and then distilled bulb to bulb (bp 155° C., 0.2 mm) to afford 2.61 g (74%) of the title compound as a clear, colorless oil, which was obtained as a mixture of diastereomers as indicated by the 1H NMR spectrum: 1H NMR (CDCl3) δ 1.14, 1.24, 1.26, 1.29 (4×s, 6H), 2.0-2.2 (m, 2H), 6.0-6.2 (m, 2H), 6.90 (d, 1H), 7.1-7.5 (m, 6H), 7.75 (t, 1H); IR (neat) 1742 cm-1.

Workup

  1. filtrationThe precipitated triethylamine hydrochloride was then filtered off
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was chromatographed through silica gel
  4. distillationdistilled bulb to bulb (bp 155° C., 0.2 mm)

Sources & evidence

ORD record
ord-4d59eb08c06f44e78d1103f7edd9293d
Source dataset
uspto-grants-1987_09
Patent number
US04694013

Reaction notes

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