Diisopropylamine → (4-Carboxybenzo[b]thiophen-2-yl)boronic acid

HRID 250241ノート

反応式

HRID 250241 の反応式
[Li]CCCC.C(NC(C)C)(C)C.[S:13]1[CH:17]=[CH:16][C:15]2[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:14]1=2.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C>C1COCC1>[C:22]([C:18]1[C:15]2[CH:16]=[C:17]([B:25]([OH:30])[OH:26])[S:13][C:14]=2[CH:21]=[CH:20][CH:19]=1)([OH:24])=[O:23]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 21531Triisopropyl borateHCID 1051638Benzo[b]thiophene-4-carboxylic acidHCID 178418339Butyllithium

生成物 1

HCID 67272237(4-Carboxybenzo[b]thiophen-2-yl)boronic acid収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

A solution of n-BuLi (2.5M in hexane, 1.69 mol, 676 mL) is added slowly at −78° C. to a solution of diisopropylamine (1.69 mol, 236 mL) in 2 L of anhydrous THF. The mixture is stirred for 30 min. A solution of benzo[b]thiophene-4-carboxylic acid (0.8 mol, 143 g) in 2 L of anhydrous THF is added slowly and the mixture is allowed to reach 0° C. The reaction is cooled to −30° C. and the triisopropyl borate (2 mol, 463 mL) is added slowly. The cooling bath is removed and the mixture is allowed to reach room temperature. The reaction is quenched with 1.3 L of concentrated HCl and 1 L of water. The mixture is stirred overnight. The organic solvent is removed under reduced pressure. The precipitate is collected by filtration, washed with water, and dried under vacuum to yield the title compound (170.5 g, 96%). ES/MS m/e 221 (M−1).

後処理

  1. customto reach 0° C
  2. customThe cooling bath is removed
  3. customto reach room temperature
  4. customThe reaction is quenched with 1.3 L of concentrated HCl and 1 L of water
  5. stirringThe mixture is stirred overnight
  6. customThe organic solvent is removed under reduced pressure
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with water
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-0acf80ccbd0c42a4a68f85c323069aac
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

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