Water → 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 38237

반응식

HRID 38237 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.Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

According to Scheme 13 Step 1: A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (7.38 mmol, 1.43 g), 1-(chloromethyl)-4-methoxybenzene (7.38 mmol, 1.00 mL) and K2CO3 (7.38 mmol, 1.02 g) in acetonitrile (10 mL) was heated at 80° C. for 5 hours. Water was added and the aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4, was filtered and was concentrated under reduced pressure to afford 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (6.68 mmol, 2.10 g, 91%) as a yellow oil.

후처리

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9f37a4b9f51f466a9179e8405e328ece
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524718B2

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