Sodium Chloride → cis-4-(4-Hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acid

HRID 2225479ノート

反応式

HRID 2225479 の反応式
C([O-])=O.[NH4+].[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([O:23]CC=C)=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31].[Cl-].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31]

参加物

6

反応物 3

HCID 5234Sodium ChlorideHCID 2723923Ammonium formateHCID 67757825Allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

生成物 1

HCID 67757505cis-4-(4-Hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acid収率 14.4%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

0.2 g of bis(triphenylphosphine)palladium dichloride and 4 g of ammonium formate were added to a solution of 6.2 g of allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate (Example 10) in 80 ml of THF. The solution was reacted for 20 hours under an argon stream, while it was refluxed. After reaction, 150 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 70 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Then, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:2, the solvent was removed in vacuo, yielding 0.8 g of cis-4-(4-hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acid (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

後処理

  1. customThe solution was reacted for 20 hours under an argon stream
  2. temperaturewhile it was refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 70 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with an aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThen, the solvent was removed in vacuo
  9. customThe oily substance obtained
  10. washFrom the fraction eluted with hexane and ethyl acetate=1:2
  11. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-3efb9b63656341e9b835057a1d2e94c7
出典データセット
uspto-grants-1994_09
特許番号
US05344845

反応ノート

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