Ethanol → HCID 15278473, compound

HRID 129389Notes

Reaction equation

HRID 129389 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][CH2:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:23](N(CC)CC)[CH3:24].ClC(OCC)=O.C(O)C>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:23][CH3:24])=[O:9])=[C:6]([O:11][CH2:12][C:13]2[N:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[N:18]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 15278472HCID 15278472, compound

Product 1

HCID 15278473HCID 15278473, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

1.0 g of 6-chloro-2-[(4,6-dimethoxy-2-pyrimidyl)methyloxy]benzoic acid was dissolved in 20 ml of tetrahydrofuran and cooled with ice. 0.35 g of triethylamine dissolved in 1 ml of tetrahydrofuran and 0.40 g of ethyl chloroformate dissolved in 1 ml of tetrahydrofuran were added thereto, and the mixture was stirred under ice cooling for about 30 minutes. Then, a solution of 1 g of ethanol and 0.35 g of triethylamine in 2 ml of tetrahydrofuran was added, and the temperature was raised up to room temperature in about one hour. After the removal of the solvent, the residue was purified using column chromatography to obtain 1.0 g of ethyl 6-chloro-2-[(4,6-dimethoxy-2-pyrmidyl)methyloxy]benzoate (yield 92%).

Workup

  1. temperaturecooled with ice
  2. additionwere added
  3. customAfter the removal of the solvent
  4. customthe residue was purified

Sources & evidence

ORD record
ord-944409862daa474487d0e8a8e8e56bf0
Source dataset
uspto-grants-1995_11
Patent number
US05468721

Reaction notes

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