2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

HRID 895672

반응식

HRID 895672 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][O:11][CH3:12])[C:4]=1[O:13][CH3:14].C([Li])CCC.C(O[B:24]1[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]1)(C)C>C(OCC)C>[CH3:14][O:13][C:4]1[C:5]([O:9][CH2:10][O:11][CH3:12])=[C:6]([B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 109979631,2-Dimethoxy-3-(methoxymethoxy)benzeneHCID 178418339Butyllithium

생성물 1

HCID 223807722-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

The MOM-protected phenol 1 (10 g; 0.0505 mol) was dissolved 1000 ml of dry diethyl ether and cooled to −78° C. A solution of n-butyl lithium (22.2 ml of 2.5 M) was then added via syringe. The cooling bath was removed and the solution was allowed to warm to room temperature. After stirring the solution at room temperature for two hours, a yellow precipitate was observed. The mixture was cooled to −78° C., and 15 ml of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.080 mol) was added via syringe. The cooling bath was removed after two hours. Stirring was continued for four hours at room temperature. The mixture was then poured into 300 ml of water and extracted several times with diethyl ether (3×300 ml), dried (Na2SO4), and concentrated to a yellow oil (12.37 g, 76%) that was used without further purification: 1H NMR: (300 MHz, CDCl3): 7.46 (d, 1H, J=8.4 Hz); 6.69 (d, 1H, J=8.4 Hz); 5.15 (s, 2H); 3.87 (s, 3H); 3.83 (s, 3H); 1.327 (s, 12H).

후처리

  1. customThe cooling bath was removed
  2. temperatureto warm to room temperature
  3. temperatureThe mixture was cooled to −78° C.
  4. customThe cooling bath was removed after two hours
  5. stirringStirring
  6. waitwas continued for four hours at room temperature
  7. additionThe mixture was then poured into 300 ml of water
  8. extractionextracted several times with diethyl ether (3×300 ml)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated to a yellow oil (12.37 g, 76%) that
  11. customwas used without further purification

출처 및 근거

ORD 기록
ord-67d538637692469ba23701d8b5ff3965
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916832B2

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