Potassium Iodide → Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate

HRID 631373노트

반응식

HRID 631373 반응식
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[CH2:17]([O:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

생성물 1

HCID 22667156Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate수율 77.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
92.5 °C

실험 절차

To solution of methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (13.0 g, 0.0572 mol) in DMF (120 mL) and benzyl chloride (7.23 ml, 0.0629 mol), K2CO3 (8.69 g, 0.0629 mol) and potassium iodide (0.949 g, 0.0057 mol) were added. The reaction mixture was heated at 90-95° C. overnight. The solvent was evaporated under vacuum and the residue was taken in ethyl acetate and washed with water and brine. After drying over MgSO4, the solution was concentrated ad purified on silica gel column to yield methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (13.99 g, 77% yield). 1HNMR (DMSO-d6): δ 7.66 (1H, s), 7.40 (6H, m), 5.27 (2H, s), 3.83 (3H, s), 3.80 (3H, s). LC-MS (ESI) m/z 318 (M+H)+.

후처리

  1. customThe solvent was evaporated under vacuum
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution was concentrated ad
  5. custompurified on silica gel column

출처 및 근거

ORD 기록
ord-006e04c5f87743a5919f4eeaec6a8f5b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

반응 노트

불러오는 중…