4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 2-(2-Dodecylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 1087319노트

반응식

HRID 1087319 반응식
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CO[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:24][CH2:25][C:26]([CH3:29])([CH3:28])[N:27]=1>O1CCCC1>[CH2:1]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:24][CH2:25][C:26]([CH3:29])([CH3:28])[N:27]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

4

반응물 2

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 178443215HCID 178443215, 화합물

생성물 1

HCID 140975692-(2-Dodecylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil.

후처리

  1. temperatureThe solution was cooled in an ice water bath
  2. customquenched with aqueous ammonium chloride (100 ml)
  3. extractionThe reaction product was extracted into diethyl ether (100 ml)
  4. washthe organic phase was washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the organic phase
  7. customafforded a colorless oil which
  8. customwas purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant

출처 및 근거

ORD 기록
ord-44759a1e620d4bbf9690fa11b7f9576f
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034537

반응 노트

불러오는 중…