p-Bromophenyl octyl ether → 2-[4-(Octyloxy)-phenyl]-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine

HRID 1030028

반응식

HRID 1030028 반응식
[Mg].[CH2:2]([O:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:21][N:20]=1.C(=O)([O-])O.[Na+]>C(OCC)C.CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[CH2:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[CH:21][N:20]=2)=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

참가 물질

8

반응물 4

HCID 145298p-Bromophenyl octyl etherHCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 221273782-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

생성물 1

HCID 198212452-[4-(Octyloxy)-phenyl]-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine수율 67.2%

시약·촉매·용매 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A Grignard reagent solution prepared from 0.8 g of magnesium, 10.3 g of (4-bromophenyl) octyl ether and 50 ml of tetrahydrofuran was added dropwise at 0°-5° C. within 30 minutes to a mixture of 7.5 g of crude 2-chloro-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine, 75 ml of tetrahydrofuran and 0.36 g of 1,3-bis(diphenylphosphino)-propanenickel-(II) chloride. The reaction mixture was stirred for 3 hours, left to stand overnight, then adjusted to pH 8 with aqueous sodium hydrogen carbonate solution and diluted with diethyl ether. The organic phase was washed neutral with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue (14.6 g) on 210 g of silica gel with hexane/ethyl acetate (vol. 4:1) yielded 8.8 g of 2-[4-(octyloxy)-phenyl]-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine.

후처리

  1. waitleft
  2. waitto stand overnight
  3. washThe organic phase was washed neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customChromatographic purification of the residue (14.6 g) on 210 g of silica gel with hexane/ethyl acetate (vol. 4:1)

출처 및 근거

ORD 기록
ord-353edb4686bd4b7699d7958b0d957b13
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104569

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