Hexanoyl chloride → Methyl 5-pentyl-1,3-oxazole-4-carboxylate

HRID 485027Notes

Reaction equation

HRID 485027 reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[C-:8].[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>O1CCCC1>[CH2:18]([C:19]1[O:20][CH:8]=[N:7][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH2:17][CH2:16][CH2:15][CH3:14]

Participants

5

Reactant 3

HCID 67340Hexanoyl chlorideHCID 547815Methyl isocyanoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20271341Methyl 5-pentyl-1,3-oxazole-4-carboxylateYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50.1 g of potassium t-butoxide are dissolved in 500 ml of tetrahydrofuran, and 37.0 g of methyl α-isocyanoacetate are added dropwise thereto at -50° C. to -40° C. The mixture is stirred at the same temperature for 30 minutes. 50.0 g of n-caproyl chloride are gradually added to the mixture at -50° C. to -40° C., and the mixture is stirred at the temperature below -30° C. for 20 hours. After the reaction, the mixture is treated in the same manner as described in Preparation 1-(1). 40 g of 5-n-pentyl-4-methoxycarbonyloxazole are thereby obtained as oil. Yield: 54.3%.

Workup

  1. customat -50° C. to -40° C
  2. stirringthe mixture is stirred at the temperature below -30° C. for 20 hours
  3. customAfter the reaction
  4. additionthe mixture is treated in the same manner
  5. customas described in Preparation 1-(1)

Sources & evidence

ORD record
ord-23f96300fb884965b265596c44601df0
Source dataset
uspto-grants-1985_08
Patent number
US04535089

Reaction notes

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