Tert-Butyl hypochlorite → 7-(1-Chloro-2,6-dioxocyclohexyl)-5-heptynoic acid methyl ester

HRID 973101Notes

Reaction equation

HRID 973101 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]1=[O:17].[Cl:19]OC(C)(C)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][C:10]1([Cl:19])[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]1=[O:17]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 13873492Methyl 7-(2,6-dioxocyclohexyl)hept-5-ynoate

Product 1

HCID 544782317-(1-Chloro-2,6-dioxocyclohexyl)-5-heptynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

7-(2,6-Dioxocyclohexyl)-5-heptynoic acid methyl ester (21.0 g), prepared as described in Example 13, is dissolved in chloroform (300 ml) cooled to 20° C and t-butyl hypochlorite (9.5 g) in chloroform (10 ml) is added to the well stirred solution over a period of 15 minutes. The mixture is stirred for another 30 minutes and allowed to warm up to room temperature. Removal of the solvent affords 7-(1-chloro-2,6-dioxocyclohexyl)-5-heptynoic acid methyl ester, γmaxFilm 1730, 1720.

Workup

  1. stirringThe mixture is stirred for another 30 minutes
  2. temperatureto warm up to room temperature
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-a3a43de654304c7c82fb0bc39e7c15d9
Source dataset
uspto-grants-1977_10
Patent number
US04054741

Reaction notes

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