Diethyl Ether → HCID 20344550, compound

HRID 2049837Notes

Reaction equation

HRID 2049837 reaction equation
[Cl:1][C:2](Cl)([Cl:8])C(OCC)=O.[C:10]1([S:16][CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+].CCOCC>O>[C:10]1([S:16][CH:17]2[CH:18]([C:19]([O:21][CH3:22])=[O:20])[C:2]2([Cl:8])[Cl:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10588Ethyl trichloroacetateHCID 10942334Sodium MethoxideHCID 54247095Methyl 3-(phenylsulfanyl)prop-2-enoate

Product 1

HCID 20344550HCID 20344550, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Freshly distilled ethyl trichloroacetate (164.8 g, 0.86 mmol) is added all at once to a cold (-50° ) stirred mixture of dry methyl 3-phenylthio-2-propenoate (155.4 g, 0.8 mol), dry olefin-free pentane (600 ml) and sodium methoxide (50 g, 0.92 mol). The cold mixture is allowed to stir under nitrogen at -50° for 4 hr and is then warmed slowly to RT over a period of 24 hr. Ether and water are added, and the organic layer is separated, washed with water, dried over calcium sulfate and solvent is removed under vacuum. The residue is purified by chromatography on silica gel, giving methyl 3-phenylthio-2,2-dichlorocyclopropanecarboxylate.

Workup

  1. stirringto stir under nitrogen at -50° for 4 hr
  2. customthe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over calcium sulfate and solvent
  5. customis removed under vacuum
  6. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fab50d5817784445aca9e2e39ebf7358
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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