Methanol → HCID 9884617, 화합물

HRID 1057662노트

반응식

HRID 1057662 반응식
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]#[N:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 887Methanol2회HCID 18671671[(9-Benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

생성물 1

HCID 9884617HCID 9884617, 화합물수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

To a mixture of [(9-benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.9 g, 2.6 mmol) in dry THF (50 mL) is added borane-methylsulfide complex (0.75 mL, 7.9 mmol). The mixture is heated at 40° C. overnight. Methanol is slowly added to mixture until addition of methanol did not evolve gas. The solvents are removed under reduced pressure. Methanol (50 mL) is added to the residue then removed under reduced pressure. Methanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue. The mixture is heated at 75° C. for 2.5 h. The mixture is neutralized with saturated potassium carbonate and partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography, silica gel (100 mL) using CH2Cl2: CH3OH (95:5) as eluent gave 0.52 g (58%) of the title compound; 1H NMR (DMSO-d6) δ2.48, 3.8, 4.12, 5.59, 6.69, 6.8, 7.14, 7.2, 8.03; Anal. Calcd for C22H22N2O2: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.00; H, 6.54; N, 7.92.

후처리

  1. additionis added borane-methylsulfide complex (0.75 mL, 7.9 mmol)
  2. customThe solvents are removed under reduced pressure
  3. additionMethanol (50 mL) is added to the residue
  4. customthen removed under reduced pressure
  5. additionMethanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue
  6. temperatureThe mixture is heated at 75° C. for 2.5 h
  7. custompartitioned between water and ethyl acetate
  8. customThe layers are separated
  9. washthe organic layer washed twice with brine
  10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3fd934a8df21413d88b445482b5f48d5
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

반응 노트

불러오는 중…