Triphenylphosphine → 4-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol ester

HRID 545152ノート

反応式

HRID 545152 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[N:17]1([CH2:23][CH2:24]O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:11][CH:10]=2)[O:5]1

参加物

6

反応物 4

HCID 11776Triphenylphosphine2 回HCID 611632-Morpholinoethanol2 回HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 5363146Diisopropyl azodicarboxylate2 回

生成物 1

HCID 46259104-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol ester収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirring solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenol (2.55 g, 11.58 mmol), 2-morpholin-4-ylethanol (1.60 mL, 1.73 g, 13.2 mmol) and triphenyl phosphine (3.64 g, 13.9 mmol) in methylene chloride (60 mL) at 0° C. was added dropwise DIAD (2.82 g, 13.9 mmol). The reaction was allowed to warm to room temperature and stir overnight. After 18 hours, additional portions of triphenyl phosphine (1.51 g, 5.8 mmol), 2-morpholin-4-ylethanol (0.70 mL, 5.8 mmol), and DIAD (1.17 g, 5.8 mmol) were added. After stirring an additional 2 hours at room temperature the reaction was concentrated and the residue purified by flash chromatography (5% to 25% EtOAc in CHCl3) to provide the product as a white solid (2.855 g, 74%).

後処理

  1. waitAfter 18 hours
  2. stirringAfter stirring an additional 2 hours at room temperature the reaction
  3. concentrationwas concentrated
  4. customthe residue purified by flash chromatography (5% to 25% EtOAc in CHCl3)

出典と根拠

ORDレコード
ord-ff792bd3bca84f348d58f83c8ca8a238
出典データセット
uspto-grants-2011_05
特許番号
US07935697B2

反応ノート

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