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

HRID 1030028

反応式

HRID 1030028 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-353edb4686bd4b7699d7958b0d957b13
出典データセット
uspto-grants-1992_04
特許番号
US05104569

関連ノート

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