Trityl chloride → 4-Trityloxy-2-cyclopentenone

HRID 2563

반응식

HRID 2563 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 109914404-Trityloxy-2-cyclopentenone수율 37%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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) δ7.5 (m, 6H), 7.3 (m, 9H), 6.85 (dd, 1H), 6.05 (d, 1H), 4.8 (m, 1H), 2.1 (m, 2H); 13C NMR (CDCl3) δ206.6, 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dc292523a26943b1a8ab4fada76c991b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728899

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