Triethylamine → Methyl 2-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 880517Notes

Reaction equation

HRID 880517 reaction equation
[CH2:1](N(CC)CC)[CH3:2].CCl.[NH2:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13].Cl.[CH2:18](OC(=N)C)C>ClCCl>[CH3:1][C:2]1[O:13][CH2:12][CH:11]([C:14]([O:16][CH3:18])=[O:15])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 86654677HCID 86654677, compound

Product 1

HCID 10844497Methyl 2-methyl-4,5-dihydro-1,3-oxazole-4-carboxylateYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.86 g, 58.01 mmol) was added to a suspension of L-serine methyl hydrochloride (4.5 g, 29.03 mmol) and ethylacetimidate hydrochloride (4.3 g, 34.95 mmol) in dichloromethane (40 mL) at 0° C. over a period of 20 min. The mixture was then stirred at ambient temperature for 18 h. The suspension was filtered and washed with diethyl ether. The solid which precipitated from the filtrate was again filtered and washed with diethyl ether. The resulting filtrate was dried over anhydrous sodium sulfate and concentrated in vacuo to afford methyl 2-methyl-4,5-dihydrooxazole-4-carboxylate (3 g, 72%) as a liquid.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with diethyl ether
  3. customThe solid which precipitated from the filtrate
  4. filtrationwas again filtered
  5. washwashed with diethyl ether
  6. dry with materialThe resulting filtrate was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ba83008ff2e46b78f47f806272b42eb
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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