2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

HRID 467548

반응식

HRID 467548 반응식
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH:10]=2)[O:3]1

참가 물질

4

반응물 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 574776664-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.2 g, 41 mmol) in NMP (60 mL) was added K2 CO3 (12 g, 82 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (7.8 mL, 43 mmol) in sequence. The reaction mixture was stirred at r.t. under N2 for 16 h. Then, the reaction mixture was diluted and filtered, and then the filtrate was diluted with EtOAc (300 mL). The resulting solution was washed with sat. NaHCO3 (aq) (3×200 mL), H2O (4×200 mL), brine (1×200 mL), dried over Na2SO4, filtered, concentrated and dried in vacuo to yield intermediate Int-15a (11.4 g, 86%) as a clear yellowish oil.

후처리

  1. additionThen, the reaction mixture was diluted
  2. filtrationfiltered
  3. additionthe filtrate was diluted with EtOAc (300 mL)
  4. washThe resulting solution was washed with sat. NaHCO3 (aq) (3×200 mL), H2O (4×200 mL), brine (1×200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo
  9. customto yield intermediate Int-15a (11.4 g, 86%) as a clear yellowish oil

출처 및 근거

ORD 기록
ord-24b076b08e6141dc8d360f7e8d15dcd4
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623857B2

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