Dichloromethane → CYCLOPROPANECARBOXYLIC ACID, 2-(4-METHOXYPHENYL)-, (1R,2R)-REL-

HRID 840704ノート

反応式

HRID 840704 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1.[N+](=C[C:14]([O:16]CC)=[O:15])=[N-].Cl[CH2:20]Cl>CCCC(C)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl.C([C@H]1COC(C2C=CC=C(C3OC[C@H](C(C)C)N=3)N=2)=N1)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:20][C@H:10]2[C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 6344Dichloromethane2 回HCID 12192Ethyl diazoacetateHCID 125074-Methoxystyrene

生成物 1

HCID 10702898CYCLOPROPANECARBOXYLIC ACID, 2-(4-METHOXYPHENYL)-, (1R,2R)-REL-

試薬・触媒・溶媒 3

HCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridine触媒HCID 10908223Dichloro(p-cymene)ruthenium(II) dimer触媒HCID 78922-Methylpentane溶媒

実験手順

To a solution of dichloro(p-cymene)ruthenium (II) dimer (250 mg) and 2,6-bis[(4S)isopropyl-2-oxazolin-2-yl]pyridine (240 mg) in dichloromethane (150 ml) was added 1-methoxy-4-vinylbenzene (25 g). To this solution was added ethyl diazoacetate (5.0 g) in dichloromethane (20 ml) over 6 hours. The solution was maintained at room temperature for 18 hours then diluted with i-hexane (200 ml) and passed through a plug of silica (50 g) washing with i-hexane/dichloromethane (1:1, 250 ml). The filtrate was concentrated and the residue taken into methanol (100 ml). Lithium hydroxide (4.0 g) in water (10 ml) was added and the mixture heated at reflux for 4 hours. The resulting solution was concentrated to give a solid which was washed with 1:1 ether/i-hexane (100 ml). The solid was then triturated with 2N HCl and the white precipitate collected to give the subtitle compound (5.1 g).

後処理

  1. washwashing with i-hexane/dichloromethane (1:1, 250 ml)
  2. concentrationThe filtrate was concentrated
  3. additionLithium hydroxide (4.0 g) in water (10 ml) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 4 hours
  6. concentrationThe resulting solution was concentrated
  7. customto give a solid which
  8. washwas washed with 1:1 ether/i-hexane (100 ml)
  9. customThe solid was then triturated with 2N HCl
  10. customthe white precipitate collected

出典と根拠

ORDレコード
ord-48102d6eeff147658cfc5eb0bb70a6f7
出典データセット
uspto-grants-2002_04
特許番号
US06369064B1

反応ノート

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