Diethyl Ether → (1S,4R)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-cyclopenten-1-YL acetate

HRID 2557

反応式

HRID 2557 の反応式
[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(OCC)C.C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1>[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([O:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-HCID 21226206Ethyl acetate hexane

生成物 1

HCID 10999690(1S,4R)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-cyclopenten-1-YL acetate収率 98%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (1 g, 4.67 mmol, prepared in example 10) in pyridine (20 mL) and treat with acetic anhydride (2 mL). Stir the reaction overnight. Dilute the reaction with diethyl ether (100 mL), wash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum to provide the title compound (1 g, 98% yield) Rf =0.5 (5% ethyl acetate/hexane) [α]20D =+1.3°, (c=1.00, chloroform), 1H NMR (CDCl3)δ5.9 (m, 1H), 5.5 (m, 1H), 4.7 (m, 1H), 2.8 (m, 1H), 2.05 (s, 3H), 1.6 (m, 1H), 0.91 (s, 9H), 0.09 (s, 6H); 13C NMR (CDCl3) δ170.8, 138.8, 131.1, 76.9, 74.8, 41.1, 25.8, 21.1, 18.1, -4.7, -4.6; IR (neat) νmax 2955, 2932, 2859, 1739, 1369, 1240, 1105, 1062, 1049 cm-1 ; CIMS m/e (% relative intensity) 256 (M+H+, 7), 197 (M+H+ --AcOH, 100).

後処理

  1. customthe reaction overnight
  2. additionDilute
  3. washwash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL)
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

出典と根拠

ORDレコード
ord-cd21d400e0ca42969b8c9e946aa2ff9e
出典データセット
uspto-grants-1998_03
特許番号
US05728899

関連ノート

読み込み中…