2-Methyl-2-butene → HCID 12045064, compound

HRID 1829710Notes

Reaction equation

HRID 1829710 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][C:6]1[C:7]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH:16]=[O:17])[CH:12]=[CH:11]2)=[O:4].P([O-])(O)(O)=[O:28].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>ClCCl.C(O)(C)(C)C.O>[CH3:1][C:2]([CH3:25])([CH3:26])[C:3]([O:5][C:6]1[C:7]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([C:16]([OH:28])=[O:17])[CH:12]=[CH:11]2)=[O:4]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 12045063HCID 12045063, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 12045064HCID 12045064, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

A mixture of the preceding aldehyde 4 (step 3) (3.5 g, 10 mmol), sodium dihydrogen phosphate (1.7 g, 12 mmol), 2-methyl-2-butene (6.1 ml, 57 mmol) and sodium chlorite (2.6 g, 29 mmol) is stirred at 20° C. in 160 ml of a 5/1 tert-butanol/water mixture and 30 ml of dichloromethane for 12 hours. The reaction medium is concentrated under reduced pressure. The residue is chromatographed on a silica column, eluting with pure ethyl acetate so as to give 2.4 g (64%) of 8-(2,2-dimethylpropionyloxy)-7-butoxycarbonylquinoline-2-carboxylic acid 5 in the form of white crystals.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe residue is chromatographed on a silica column
  3. washeluting with pure ethyl acetate so as

Sources & evidence

ORD record
ord-6a6fdc7999104437b71d9fc29ec10a17
Source dataset
uspto-grants-2006_06
Patent number
US07064133B2

Reaction notes

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