Toluene → 3-[2-(3-Chlorophenyl)ethyl]-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-pyridine

HRID 270663

반응식

HRID 270663 반응식
C1C[O:4][CH2:3]C1.[Li+].C[CH:8]([N-:10][CH:11]([CH3:13])[CH3:12])[CH3:9].O1[CH2:18][CH2:17][N:16]=C1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Cl.[C:28]1([CH3:34])C=CC=C[CH:29]=1>O>[Cl:19][C:20]1[CH:21]=[C:22]([CH2:23][CH2:34][C:28]2[C:9]([C:8]3[O:4][CH2:3][C:11]([CH3:12])([CH3:13])[N:10]=3)=[N:16][CH:17]=[CH:18][CH:29]=2)[CH:25]=[CH:26][CH:27]=1

참가 물질

7

반응물 5

HCID 1140TolueneHCID 8028Tetrahydrofuran2회HCID 12103m,alpha-DichlorotolueneHCID 68157OxazolineHCID 2724682Lithium diisopropylamide

생성물 1

HCID 102677853-[2-(3-Chlorophenyl)ethyl]-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-pyridine수율 80.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

521.7 ml of anhydrous THF and 521.7 ml of 2M LDA solution (1.04 mol) are placed in a 3-litre jacketed reactor equipped with a mechanical stirrer and thermometer, and maintained under a nitrogen atmosphere, the internal temperature is brought to −5° C. and a solution consisting of 158.8 g of oxazoline (0.835 mol) and 834.7 ml of anhydrous THF is then added slowly, keeping the temperature at about 0° C. After adding a few drops of solution, a strong blue-violet colour is obtained. The total addition time is about one hour. 154.6 g (0.96 mol) of 3chlorobenzyl chloride are then added over about 1.5 hours, while still maintaining the temperature at 0° C. At the end of the reaction, 521.7 g of water are added while bringing the temperature to 20-25° C. The two phases are then separated and the organic phase is evaporated to give an oil. The crude product thus obtained is taken up in toluene and filtered through Tonsil. The filtrate is concentrated to give 268.1 g of an oil with an HPLC titre of 79%. 91.8% conversion, yield=80.2%

후처리

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer, and maintained under a nitrogen atmosphere
  3. customis brought to −5° C.
  4. additionis then added slowly
  5. customat about 0° C
  6. customa strong blue-violet colour is obtained
  7. additionThe total addition time
  8. additionare added
  9. customto 20-25° C
  10. customThe two phases are then separated
  11. customthe organic phase is evaporated
  12. customto give an oil
  13. customThe crude product thus obtained
  14. filtrationfiltered through Tonsil
  15. concentrationThe filtrate is concentrated

출처 및 근거

ORD 기록
ord-2e436d3a1b6946028cfc74c1f83c2db0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449583B2

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