Trityl chloride → 4-Trityloxy-2-cyclopentenone

HRID 2393906

Reaktionsgleichung

Reaktionsgleichung von HRID 2393906
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[OH:32][CH:33]1[CH2:37][C:36](=[O:38])[CH:35]=[CH:34]1>C(Cl)Cl>[C:1]([O:38][CH:36]1[CH2:37][C:33](=[O:32])[CH:34]=[CH:35]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 41691604-Hydroxycyclopent-2-en-1-one

Produkt 1

HCID 109914404-Trityloxy-2-cyclopentenoneAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of trityl chloride (3.44 g, 12.3 mmol) in methylene chloride (20 mL) is treated sequentially with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.2 mL, 14.7 mmol, DBU) and 4-hydroxy-2-cyclopentenone (1.01 g, 10.0 mmol, in 5 mL of methylene chloride, prepared in example 1). The reaction is stirred for 3 days at room temperature and then poured onto ice (approximately 25 mL). The phases are separated and the organic phase is washed with water (25 mL). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 10-20% ethyl acetate/hexane) to provide the title compound (1.26 g, 36 %) as a pale yellow oil; 1H NMR (CDCl3) δ 7.5 (m, 6 H), 7.3 (m, 9 H), 6.85 (dd, 1 H), 6.05 (d, 1 H), 4.8 (m, 1 H), 2.1 (m, 2 H); 13C NMR (CDCl3) δ 206.6, 162.9, 144.3, 135.2, 128.8, 128.4, 127.7, 88.2, 73.1, 43.4; IR (KBr) νmax 3061, 1719, 1491, 1449, 1352, 1181, 1107, 1053 cm-1.

Aufarbeitung

  1. additionpoured onto ice (approximately 25 mL)
  2. customThe phases are separated
  3. washthe organic phase is washed with water (25 mL)
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by column chromatography (silica gel, 10-20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d78ddd782e134d5496dd92df1b0ba3d9
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808112

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