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Piperidine → Tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate

HRID 2390273
ノート
印刷プレビュー

反応式

HRID 2390273 の反応式
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:24]=1)#[CH:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1CCCCC1>O.CC(C)=O.[Pd](Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:22]#[C:21][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 565942671-Ethynyl-3-(propylsulfonyl)benzeneHCID 58522023tert-Butyl[(1-bromo-2-naphthyl)oxy]acetate2 回

生成物 1

HCID 58521954Tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate

試薬・触媒・溶媒 3

HCID 24290
Palladium Chloride
触媒
HCID 180Acetone溶媒
HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of (1-bromo-naphthalen-2-yloxy)-acetic acid tert-butyl ester (Intermediate 217; 500 mg; 1.48 mmol), 1-ethynyl-3-(propane-1-sulfonyl)-benzene (618 mg; 2.97 mmol) and PPh3 (39 mg; 0.15 mmol) in water (4.40 ml) and Acetone (5.6 ml) was treated with palladium(II) chloride (13 mg; 0.07 mmol) and piperidine (295 μl; 2.97 mmol) and heated at 60° C. for 2 days. The reaction mixture was extracted with EtOAc, the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a yellow sticky solid.

後処理

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialthe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by flash column chromatography (silica)
  5. washeluting with cyclohexane containing
  6. temperatureincreasing amounts of EtOAc

出典と根拠

ORDレコード
ord-901b093ed95c443f82efc5ecf792a660
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273769B2

反応ノート

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