Hydrochloric Acid → (4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid

HRID 1518248ノート

反応式

HRID 1518248 の反応式
Br[C:2]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:3]=1[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[Li]CCCC.[B:27](OC(C)C)([O:32]C(C)C)[O:28]C(C)C.Cl>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:2]([B:27]([OH:32])[OH:28])=[C:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 67346559HCID 67346559、化合物HCID 178418339Butyllithium

生成物 1

HCID 67345879(4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

[(2-bromo-5-methoxybenzyl)oxy](triisopropyl)silane (1 eq.) was dissolved in anhydrous THF (0.43M solution) and the solution was cooled to −78° C. A solution of n-BuLi (1.6M in hexanes, 1.05 eq.) was added and the resulting mixture was left stirring for 1 h at −78° C. Then triisopropyl borate (50% in THF, 1.3 eq.) was added dropwise and the mixture was allowed to warm to RT overnight. 1N HCl was added and the resulting mixture was left stirring at RT for 30 min. THF was removed in vacuo and replaced with Et2O. The organic phase was washed with water and with brine, then dried over Na2SO4 and evaporated in vacuo. The product was obtained as a colorless oil (64% yield, 65% pure) which was used without further purification in the next reaction.

後処理

  1. waitthe resulting mixture was left
  2. temperatureto warm to RT overnight
  3. waitthe resulting mixture was left
  4. stirringstirring at RT for 30 min
  5. customTHF was removed in vacuo
  6. washThe organic phase was washed with water and with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo
  9. customThe product was obtained as a colorless oil (64% yield, 65% pure) which
  10. customwas used without further purification in the next reaction

出典と根拠

ORDレコード
ord-6bd34ecbd1284eb5b8f2f0048d99f7dc
出典データセット
uspto-grants-2012_07
特許番号
US08232390B2

反応ノート

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