Water → 3-Phenoxybenzyl (1S,3R)-3-(2-chloro-3,3,3-trifluoro-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate-rel-

HRID 1155666Notes

Reaction equation

HRID 1155666 reaction equation
[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[O:16]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][OH:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1.O>C(Cl)Cl>[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7]([O:27][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:24]=2)=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 262953-Phenoxybenzyl alcoholHCID 86736786trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 1564503-Phenoxybenzyl (1S,3R)-3-(2-chloro-3,3,3-trifluoro-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate-rel-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1.8 g (0.007 mole) of trans-3-[2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chloride in 10 ml of methylene chloride at ambient temperature was added a solution of 1.6 g (0.008 mole) of 3-phenoxybenzyl alcohol and 0.73 g (0.009 mole) of pyridine in 5 ml of methylene chloride. Upon complete addition the reaction mixture was stirred at ambient temperature for 3 hours, then poured into 50 ml of water. The organic layer was separated, and the aqueous layer was extracted with three portions of 50 ml each of methylene chloride. The combined extracts were dried with sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to a residual oil. Volatile components were removed from the oil at 125° C./0.05 mm using a Kugelrohr distillation system. The pot residue was 99% 3-phenoxybenzyl trans-3-[2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate, as determined by gas chromatographic analysis. The weight of product was 2.0 g. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. additionUpon complete addition the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with three portions of 50 ml each of methylene chloride
  4. dry with materialThe combined extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure to a residual oil
  7. customVolatile components were removed from the oil at 125° C./0.05 mm
  8. distillationa Kugelrohr distillation system

Sources & evidence

ORD record
ord-a3c76d51fe714e99927e906a8131e5fb
Source dataset
uspto-grants-1982_06
Patent number
US04332815

Reaction notes

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