Trimethylsilyldiazomethane → Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

HRID 1508490노트

반응식

HRID 1508490 반응식
[C:1]([C:4]1[CH:5]=[C:6]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[O:7][CH:8]=1)([OH:3])=[O:2].[CH3:18][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:12][C:11]1([CH3:13])[C:14]([CH3:16])([CH3:15])[O:17][B:9]([C:6]2[O:7][CH:8]=[C:4]([C:1]([O:3][CH3:18])=[O:2])[CH:5]=2)[O:10]1

참가 물질

5

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 467390315-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylic acid

생성물 1

HCID 53217215Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

4-Carboxyfuran-2-boronic acid pinacol ester (200 mg, 0.840 mmol) was dissolved in CH2Cl2 (4 mL) and MeOH (0.444 mL). Trimethylsilyldiazomethane (0.840 mL, 1.680 mmol) was added dropwise. After 45 min, the reaction was quenched with AcOH dropwise until the yellow color disappeared. The reaction was concentrated in vacuo to give methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-furoate. 1H NMR (500 MHz, CDCl3): δ 8.20 (s, 1H); 7.37 (s, 1H); 3.84 (s, 3H); 1.36 (s, 12H).

후처리

  1. customthe reaction was quenched with AcOH dropwise until the yellow color
  2. concentrationThe reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5d3cca8ccf0940ba8a7653d6d5747f26
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221834B2

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