5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbaldehyde → [6-(1-Hydroxyethyl)pyridin-3-yl]boronic acid

HRID 510981노트

반응식

HRID 510981 반응식
[CH3:1][Mg]Cl.CC1(C)C(C)(C)[O:8][B:7]([C:12]2[CH:13]=[CH:14][C:15]([CH:18]=[O:19])=[N:16][CH:17]=2)[O:6]1>C1COCC1>[OH:19][CH:18]([C:15]1[N:16]=[CH:17][C:12]([B:7]([OH:6])[OH:8])=[CH:13][CH:14]=1)[CH3:1]

참가 물질

4

반응물 2

HCID 447548395-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbaldehydeHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 67969224[6-(1-Hydroxyethyl)pyridin-3-yl]boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1.0 M Methylmagnesium chloride in THF (0.4 mL, 0.4 mmol) was added dropwise to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbaldehyde (50 mg, 0.2 mmol, Frontier Scientific, catalog #F2110) in THF (2 mL) at 0° C. After stirring for 1 h at room temperature, the reaction was quenched with 1 N NH4Cl and was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated to give the crude [6-(1-hydroxyethyl)pyridin-3-yl]boronic acid. This was used in the next step without purification.

후처리

  1. customthe reaction was quenched with 1 N NH4Cl
  2. extractionwas extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4d264c3177ca400dab72b905c3e76638
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096600B2

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