Water → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 574059

反応式

HRID 574059 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[Li]CCCC.[OH:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].O>C1COCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:6][CH:7]=1.[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]([OH:25])([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:23]3[CH:22]=[C:21]([OH:20])[CH:34]=[CH:33][CH:32]=3)=[CH:3][CH:4]=2)=[N:12]1

参加物

8

反応物 4

HCID 962WaterHCID 830503-HydroxybenzophenoneHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

生成物 2

HCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 599879993-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

2-(4-Bromophenyl)-4,4-dimethyl-1,3-oxazoline 1 was prepared as described in Example 4. To a stirred solution of 2-(4-bromophenyl)-4,4-dimethyl-1,3-oxazoline (1.5 g, 6 mM) in anhydrous THF (10 mL) at −78° C. was added slowly n-BuLi (384 mg, 6 mM) in hexane over the period of 20 min. After that the reaction mixture was stirred at −78° C. for another 30 min. To this stirred solution was added 3-hydroxybenzophenone (534 mg, 2.7 mM) dissolved in anhy. THF (10 mL) by dropwise at −78° C. and allowed to stir at room temperature overnight. To this reaction mixture was added 20 mL of water to quench the reaction and extracted with CH2Cl2 (3×50 mL) and the combined extract was dried over anhydrous Mg2SO4. The oily residue obtained on evaporation of the solvent was purified by silica gel column chromatography using hexane/EtOAc (1:1) mixture gave 3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol (2) as colorless crystalline solid. Yield: 0.855 g (85%). Mass: 374 (MH+), 372 (M-H).

後処理

  1. dissolutiondissolved in anhy
  2. customdropwise at −78° C.
  3. stirringto stir at room temperature overnight
  4. customto quench
  5. customthe reaction
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. extractionthe combined extract
  8. dry with materialwas dried over anhydrous Mg2SO4
  9. customThe oily residue obtained on evaporation of the solvent
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fed17c506bf24ee89111b30b5c4683f4
出典データセット
uspto-grants-2015_05
特許番号
US09034798B2

関連ノート

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