2-Bromoanisole → 2-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline

HRID 354574

반응식

HRID 354574 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.BrC1C=CC=CC=1OC.[Mg].CO[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=1

참가 물질

6

반응물 4

HCID 113582-BromoanisoleHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224MagnesiumHCID 178489560HCID 178489560, 화합물

생성물 1

HCID 126110122-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Methoxyphenylmagnesium bromide, prepared from 2-bromoanisole (22.4 g, 120 mmol) and magnesium (2.9 g, 120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (20.4 g, 100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2×500 ml), dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (ethyl acetate-hexane) to provide title compound as colorless crystals (25.3 g, 90%), mp 129°-131° C.

후처리

  1. customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionThe resulting mixture was extracted with ether (2×500 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-7aa77486be2f4976a415c984f8913fa5
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04375475

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