Propanal → 5-Ethyl-4-tosyl-2-oxazoline

HRID 505573

반응식

HRID 505573 반응식
[S:1]([CH2:11][N:12]=[C:13]=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH:15](=O)[CH2:16][CH3:17].[Na].O1CCN=C1>C(O)C>[CH2:16]([CH:17]1[O:14][CH:13]=[N:12][CH:11]1[S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2])[CH3:15]

참가 물질

6

반응물 4

HCID 527PropanalHCID 68157OxazolineHCID 5360545SodiumHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzene

생성물 1

HCID 667581855-Ethyl-4-tosyl-2-oxazoline수율 81%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred suspension of tosylmethylisocyanate (TosMIC, 3.90 g, 20 mmol) and propionaldehyde (1.5 mL 20.4 mmol) in 60 mL dry ethanol, finely powdered sodium cyamide (0.098 g, 2 mmol) was added. The reaction mixture became clear and white crystals of oxazoline began to precipitate in 15 min. The reaction was continuously stirred for an additional 30 min. The mixture was filtered and the crystals were washed with ether-hexane (1:1) before drying. Compound 15 was attained in 81% yield (4.1 g). The structure was confirmed by 1H NMR in CDCl3, LC-MS: [M+1]=254. Purity was >98%.

후처리

  1. additionwas added
  2. customto precipitate in 15 min
  3. filtrationThe mixture was filtered
  4. washthe crystals were washed with ether-hexane (1:1)
  5. custombefore drying

출처 및 근거

ORD 기록
ord-97d179396b0740fb8856b9230ba3e5e7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781442B2

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