Phosphorus oxychloride → Ethyl 3-(4-iodophenyl)-3-chloro-2-ethoxycarbonylacrylate

HRID 1740083Notes

Reaction equation

HRID 1740083 reaction equation
[I:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)([Cl:32])=O>>[I:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([Cl:32])=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 53643535Diethyl 4-iodobenzoylmalonate

Product 1

HCID 21837631Ethyl 3-(4-iodophenyl)-3-chloro-2-ethoxycarbonylacrylate

Conditions

Temperature
100 °C

Procedure

A mixture of 28.3 g of diethyl 4-iodobenzoylmalonate, 14.6 g of diisopropylethylamine and 20 ml of phosphorus oxychloride was stirred at 100° C. for 2 hours and then poured over ice. The reaction mixture was extracted with diethyl ether, and the extract was dried over magnesium sulfate, treated with activated carbon, filtered and then concentrated at atmospheric pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 20.14 g of the title compound as a pale yellow liquid.

Workup

  1. additionpoured over ice
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. dry with materialthe extract was dried over magnesium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. concentrationconcentrated at atmospheric pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6514158aa5f5406ba72b8477e8bafc5c
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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