Hydrochloric Acid → 3-(4'-Chloro-4-ethylbiphen-3-yl)-1-methoxybicyclo[3.2.2]non-6-ene-2,4-dione

HRID 72278ノート

反応式

HRID 72278 の反応式
[CH3:1][O:2][C:3]12[CH2:11][CH2:10][CH:7]([CH:8]=[CH:9]1)[C:6](=[O:12])[CH2:5][C:4]2=[O:13].[C:14]1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:33][C:34]1[CH:47]=[CH:46][C:37]([C:38]2[CH:39]=[CH:40][C:41]([CH3:45])=[C:42]([Pb+3])[CH:43]=2)=[CH:36][CH:35]=1.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:33][C:34]1[CH:47]=[CH:46][C:37]([C:38]2[CH:39]=[CH:40][C:41]([CH2:45][CH3:14])=[C:42]([CH:5]3[C:6](=[O:12])[CH:7]4[CH2:10][CH2:11][C:3]([O:2][CH3:1])([CH:9]=[CH:8]4)[C:4]3=[O:13])[CH:43]=2)=[CH:36][CH:35]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 684871751-Methoxybicyclo[3.2.2]non-6-en-2,4-dioneHCID 178476525HCID 178476525、化合物

生成物 1

HCID 1317318303-(4'-Chloro-4-ethylbiphen-3-yl)-1-methoxybicyclo[3.2.2]non-6-ene-2,4-dione

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

1-methoxybicyclo[3.2.2]non-6-en-2,4-dione (0.080 g, 0.044 mmol) stirred in dry chloroform (4 ml) under a nitrogen atmosphere. 4-Dimethylaminopyridine (0.268 g, 2.2 mmol) is added, followed by dry toluene (1 ml) and the mixture is heated to 80° C. To this reaction mixture is then added 4′-chloro-4-methylbiphen-3-yl-lead triacetate (0.400 g, 0.67 mmol) portionwise, over 4 minutes, and the mixture is held at 80° C. for 3¼ hour. The reaction mixture is cooled to room temperature, acidified with dilute aqueous hydrochloric acid (10 ml), stirred vigorously for 10 minutes, then filtered through diatomaceous earth and the filter cake is washed with dichloromethane (10 ml). The filtrate is poured into a separating funnel, the organic layer collected and the aqueous phase is extracted with dichloromethane (2×10 ml). The organic fractions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The residue is taken up in N,N-dimethylformamide (approximately 2 ml) and purified by preparative reverse-phase HPLC to give 3-(4′-chloro-4-ethylbiphen-3-yl)-1-methoxybicyclo[3.2.2]non-6-ene-2,4-dione.

後処理

  1. waitthe mixture is held at 80° C. for 3¼ hour
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. washthe filter cake is washed with dichloromethane (10 ml)
  5. additionThe filtrate is poured into a separating funnel
  6. customthe organic layer collected
  7. extractionthe aqueous phase is extracted with dichloromethane (2×10 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under vacuum
  11. custompurified by preparative reverse-phase HPLC

出典と根拠

ORDレコード
ord-79992a15c617410ba1d0a1f45b24d619
出典データセット
uspto-grants-2014_09
特許番号
US08828908B2

反応ノート

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