Pivaloyl chloride → HCID 12045062, compound

HRID 1829708Notes

Reaction equation

HRID 1829708 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH:8][C:9]1[C:10]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2>N1C=CC=CC=1>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:8][C:9]1[C:10]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2)=[O:6]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 12045061HCID 12045061, compound

Product 1

HCID 12045062HCID 12045062, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10.4 ml (84 mmol) of pivaloyl chloride are added, at 0° C., to a solution of the preceding ester 2 (step 1) (11.0 g, 42 mmol) in pyridine (45 ml). After 1 hour at 20° C., the pyridine is distilled under reduced pressure, and then 20 ml of water and 50 ml of dichloromethane are added. The phases are separated and the aqueous phase extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on a silica column, eluting with a 2/1 cyclohexane/ethyl acetate mixture so as to give 11.7 g (82%) of n-butyl 8-(2,2-dimethylpropionyloxy)-2-methylquinoline-7-carboxylate 3 in the form of a yellow solid.

Workup

  1. distillationthe pyridine is distilled under reduced pressure
  2. addition20 ml of water and 50 ml of dichloromethane are added
  3. customThe phases are separated
  4. extractionthe aqueous phase extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed on a silica column
  8. washeluting with a 2/1 cyclohexane/ethyl acetate mixture so as

Sources & evidence

ORD record
ord-7ad58636f1094bfc8adeb8358aa074bd
Source dataset
uspto-grants-2006_06
Patent number
US07064133B2

Reaction notes

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