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

HRID 354574

反応式

HRID 354574 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7aa77486be2f4976a415c984f8913fa5
出典データセット
uspto-grants-1983_03
特許番号
US04375475

関連ノート

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