Acetic Acid → HCID 86755685、化合物

HRID 1872394ノート

反応式

HRID 1872394 の反応式
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=O)[CH3:4].[C:25]([OH:28])(=[O:27])[CH3:26].O1CC[CH2:31][CH2:30]1>>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6](/[C:3](/[CH3:4])=[CH:26]/[C:25]([O:28][CH2:30][CH3:31])=[O:27])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11208635HCID 11208635、化合物

生成物 1

HCID 86755685HCID 86755685、化合物

実験手順

To a suspension of sodium hydride (60% in oil, 0.37 g) in tetrahydrofuran (40 ml) was added by portions 4-acetyl-4'-n-heptylbiphenyl (2.50 g) at ambient temperature. After stirring at ambient temperature for 1 hour, to the solution was added triethyl phosphonoacetate (1.9 ml) and the mixture was heated to reflux for 5 hours. After cooling to ambient temperature, to the mixture was added acetic acid (0.53 ml) and evaporated. The residue was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (200 ml) eluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V) to give Ethyl (E)-3-[4-(4-heptylphenyl)phenyl]-2-butenoate (2.19 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling to ambient temperature, to the mixture
  4. customevaporated
  5. additionThe residue was taken up into a mixture of water and ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (200 ml)
  10. washeluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V)

出典と根拠

ORDレコード
ord-399f0cb67a604698a01a57da3cc6d975
出典データセット
uspto-grants-2000_08
特許番号
US06107458

反応ノート

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