tert-Butanol → HCID 21287969, compound

HRID 868352Notes

Reaction equation

HRID 868352 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:11](O)([CH3:14])([CH3:13])[CH3:12].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 1378606-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21287969HCID 21287969, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.3 g of 6-methylnicotinic acid, 5.0 g of 4-dimethylaminopyridine, 18.3 g of t-butyl alcohol, 22.4 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 280 ml of dichloromethane is stirred at room temperature for 2 days. The reaction mixture is washed with water, dried over magnesium sulfate, and concentrated. The residue is chromatographed on silica gel with chloroform to give 7.1 g of t-butyl 6-methylnicotinate as an oil.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-c808eedd4345449aa05091cffa6f4ee4
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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