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

HRID 874497

반응식

HRID 874497 반응식
[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

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 611632-Morpholinoethanol2회HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 5363146Diisopropyl azodicarboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e9dfdb1ce0c24ee588da2c8ed0b99059
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980890B2

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