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

反応式

HRID 895672 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-67d538637692469ba23701d8b5ff3965
出典データセット
uspto-grants-2005_07
特許番号
US06916832B2

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