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

HRID 874497

反応式

HRID 874497 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-e9dfdb1ce0c24ee588da2c8ed0b99059
出典データセット
uspto-grants-2015_03
特許番号
US08980890B2

関連ノート

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