Potassium Carbonate → 1-Cyclobutanesulfonyl-naphthalene

HRID 2212064노트

반응식

HRID 2212064 반응식
[C:1]1(S)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:12]1(Br)[CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[K+].C1OCCOCCOCCOCCOCCOC1.O[O:47][S:48]([O-:50])=O.[K+]>O.CC(C)=O.ClCCl.C(#N)C>[CH:12]1([S:48]([C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH:6]=[CH:7][CH:8]=2)(=[O:50])=[O:47])[CH2:15][CH2:14][CH2:13]1

참가 물질

11

반응물 6

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 682591-NaphthalenethiolHCID 78110BromocyclobutaneHCID 516893Potassium BicarbonateHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 219637531-Cyclobutanesulfonyl-naphthalene수율 14%

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

A mixture of naphthalene-1-thiol (1.17 g, 7.3 mmol), cyclobutyl bromide (1.45 g, 10.7 mmol), potassium carbonate (1.06 g, 7.7 mmol) and acetonitrile (20 ml) was stirred at 70° C. for 40 hours. the mixture was poured into water and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was treated with dichloromethane (30 ml), acetone (5 ml), 10% aqueous potassium bicarbonate and 18-crown-6 (100 mg, 0.4 mmol) and a solution of Oxone™ (10 g) in water (100 ml) was added. After completion, the layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-ethyl acetate) to give the title product (257 mg, 14%).

후처리

  1. extractionextracted into ethyl acetate
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customAfter completion, the layers were separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified on silica (i-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-9f3055e764ae41d48e80290051e6bc57
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101892B2

반응 노트

불러오는 중…