Hydrochloric Acid → (3s)-3-(Tert-butyldimethylsiloxy)-5-phenyl-1-pentyne

HRID 593409ノート

反応式

HRID 593409 の反応式
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[C:14]1([CH2:20][CH2:21][C@H:22]([OH:25])[C:23]#[CH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(Cl)Cl>[C:6]([Si:10]([CH3:12])([CH3:11])[O:25][C@@H:22]([CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:23]#[CH:24])([CH3:9])([CH3:8])[CH3:7]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12425712(S)-5-Phenylpent-1-yn-3-ol

生成物 1

HCID 25257491(3s)-3-(Tert-butyldimethylsiloxy)-5-phenyl-1-pentyne

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Following a procedure of Noyori (Suzuki, M. et al., J. Med. Chem. 41, 3084-3090 (1998)); Imidazole (919.1 mg, 13.5 mmol, 1.8 eq.) and t-butylchlorodimethylsilane (1.35 g, 9.0 mmol) were added to a solution of (S)-5-phenylpent-1-yn-3-ol 86 (1.2 g, 7.5 mmol, 1 eq.) in CH2Cl2 (18 ml), cooled to 0° C. The reaction mixture was then stirred at room temperature for 14 h before being poured into 1 M HCl (50 ml). The mixture was extracted with 40/60 petroleum ether (3×50 ml). The combined organic phases were washed with brine (50 ml) before being dried (MgSO4), filtered and concentrated to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (99:1), giving the title product 88 as a clear, colourless oil (1.77 g, 86%). Analytical data consistent with the literature (Kiyotsuka, Y. et al., Org. Lett. 10, 1719-1722 (2008); Sato, F. et al., EP 1211241 A1, Taisho Pharmaceutical co., LTD (2002)).

後処理

  1. extractionThe mixture was extracted with 40/60 petroleum ether (3×50 ml)
  2. washThe combined organic phases were washed with brine (50 ml)
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThis was purified by column chromatography on silica
  8. washeluting with petrol/Et2O (99:1)

出典と根拠

ORDレコード
ord-7a5b4608b20442688372341863920dc2
出典データセット
uspto-grants-2016_01
特許番号
US09242954B2

反応ノート

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