Benzyl Bromide → 2-Benzyl-5-[1,3]dioxolan-2-yl-pyridine

HRID 640539

반응식

HRID 640539 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)=[CH:12][N:11]=1>[Zn].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ni+2].O1CCCC1>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:17][CH2:18][CH2:19][O:20]2)=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 7498Benzyl BromideHCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridine

생성물 1

HCID 592551082-Benzyl-5-[1,3]dioxolan-2-yl-pyridine수율 62%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 84306Bis(triphenylphosphine)nickel(II)chloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of zinc (5.0 g, 77 mmol, highly reactive Rieke metal, 100 mL tetrahydrofuran suspension) and tetrahydrofuran (300 mL) was added dropwise benzyl bromide (7.9 mL, 66 mmol) at 0° C., which was stirred for 4 hours at the same temperature. To this suspension were added bis(triphenylphosphine)nickel (II) chloride (5.8 g, 8.8 mmol) and 2-bromo-5-[1,3]dioxolan-2-yl-pyridine (11 g, 49 mmol) described in Manufacturing Example 210-1-2, which was stirred for another 2 hours at room temperature. The reaction solution was partitioned into ethyl acetate and an ammonium chloride aqueous solution. The organic layer was separated and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1, 1:1) to obtain the title compound (7.3 g, 62%).

후처리

  1. stirringwas stirred for another 2 hours at room temperature
  2. customThe reaction solution was partitioned into ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1, 1:1)

출처 및 근거

ORD 기록
ord-308f12e17f5049c1a5d03c380b37e6cc
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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