Diethyl Ether → 2-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline

HRID 1288723ノート

反応式

HRID 1288723 の反応式
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1.[CH3:20][S:21]SC.CCOCC>C1COCC1>[Cl:6][C:7]1[C:8]([S:21][CH3:20])=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 12232Dimethyl DisulfideHCID 10798476Oxazole, 2-(3-chlorophenyl)-4,5-dihydro-4,4-dimethyl-HCID 178418339Butyllithium

生成物 1

HCID 544052592-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline収率 96.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-65 °C

実験手順

n-Butyllithium (2.5M in hexane, 4.2 ml) was added to a solution of 2-(3-chlorophenyl)-4,4-dimethyloxazoline (2 g) in THF while maintaining the temperature below -45° C. The mixture was stirred at -65° C. for 3 hours. Dimethyl disulphide (1.0 g) was added and the mixture was stirred at -65° C. for 2.5 hours and allowed to warm to room temperature. Ether was added and the mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-(3-chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline (2.35 g) as a yellow oil NMR (CDCl3) 2.0(s,6H) 3.0(s,3H) 4.65(s,2H) 7.5-8.1(m,3H).

後処理

  1. temperaturewhile maintaining the temperature below -45° C
  2. stirringthe mixture was stirred at -65° C. for 2.5 hours
  3. temperatureto warm to room temperature
  4. washthe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-a654c63c60a942f981a5513281dd6080
出典データセット
uspto-grants-1998_05
特許番号
US05747424

反応ノート

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