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

HRID 1060373

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HRID 1060373 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회HCID 8058Hexane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49a3f58f31094250ae2d5679604c4181
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521667B1

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