Sodium Hydroxide → (R)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile

HRID 1060373ノート

反応式

HRID 1060373 の反応式
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:13]1[O:15][C@H:14]1[CH2:16]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.[OH-].[Na+]>CN(C)C=O.CCCCCC.CCOCC>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]#[N:10])[C@@H:14]1[O:15][CH2:13]1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 44079952-Chloro-6-hydroxybenzonitrile

生成物 1

HCID 44186486(R)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

3-Chloro-2-cyanophenol (0.55 g, 3.58 mmol) was dissolved in 10 mL of dimethylformamide, and the solution cooled to 0° C. Sodium hydride (0.158 g, 3.94 mmol 60% in oil), washed with hexane and dimethylformamide, was added to cooled solution over a period of one minute. After stirring for 10 minutes at room temperature, (2R)-(−)-glycidyl 3-nitrobenzenesulfonate was added and stirred 16 hours. The reaction was poured into ether and dilute sodium hydroxide. The ether layer was separated and the aqueous layer extracted once more with ether. The combined ether extracts were washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.7 g of (R)-3-chloro-2-cyanophenyl glycidyl ether.

後処理

  1. additionwas added
  2. temperatureto cooled solution over a period of one minute
  3. stirringstirred 16 hours
  4. customThe ether layer was separated
  5. extractionthe aqueous layer extracted once more with ether
  6. washThe combined ether extracts were washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-49a3f58f31094250ae2d5679604c4181
出典データセット
uspto-grants-2003_02
特許番号
US06521667B1

反応ノート

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