1-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone → 3-[4-(2,3-Dihydroxy-propyl)-3,5-dimethyl-phenyl]-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one

HRID 552281

反応式

HRID 552281 の反応式
[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([CH:8]=O)=[CH:6][C:5]=1[CH3:13].[CH2:16]([C:18]1[S:22][C:21]([C:23](=[O:25])[CH3:24])=[CH:20][C:19]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:17]>C(O)C.Cl.C(O)(C)C>[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([CH2:8][CH2:24][C:23]([C:21]2[S:22][C:18]([CH2:16][CH3:17])=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=2)=[O:25])=[CH:6][C:5]=1[CH3:13]

参加物

6

反応物 2

HCID 671661641-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanoneHCID 866401714-(2,3-Dihydroxy-propyl)-3,5-dimethyl-benzaldehyde

生成物 1

HCID 592490003-[4-(2,3-Dihydroxy-propyl)-3,5-dimethyl-phenyl]-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one収率 21.7%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 3776Isopropanol溶媒

実験手順

A solution of 4-(2,3-dihydroxy-propyl)-3,5-dimethyl-benzaldehyde (64 mg, 0.308 mmol) and 1-(5-ethyl-4-phenyl-thiophen-2-yl)-ethanone (50 mg, 0.218 mmol) in ethanol (2 mL) and 5 N HCl in isopropanol (0.5 mL) is stirred at rt for 5 days. The solvent is removed in vacuo and the residue is separated by prep. HPLC. Product containing fractions are treated with sat. aq. NaHCO3 and 3 M aq. NaOH (5 mL). The mixture is stirred at rt for 1 h, then extracted with DCM. The solvent of the organic extract is removed. The residue is dissolved in THF:methanol 1:1 (5 mL) and is treated with Pd/C. The slurry is stirred at it for 16 h under 1.5 bar of H2. The mixture is filtered over celite and the filtrate is evaporated to give 3-[4-(2,3-dihydroxy-propyl)-3,5-dimethyl-phenyl]-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one (20 mg) as a colourless oil, LC-MS: tR=1.04 min, [M+1]+=423.28.

後処理

  1. customThe solvent is removed in vacuo
  2. customthe residue is separated by prep
  3. additionProduct containing fractions
  4. additionare treated with sat. aq. NaHCO3 and 3 M aq. NaOH (5 mL)
  5. extractionextracted with DCM
  6. extractionThe solvent of the organic extract
  7. customis removed
  8. dissolutionThe residue is dissolved in THF:methanol 1:1 (5 mL)
  9. additionis treated with Pd/C
  10. stirringThe slurry is stirred at it for 16 h under 1.5 bar of H2
  11. filtrationThe mixture is filtered over celite
  12. customthe filtrate is evaporated

出典と根拠

ORDレコード
ord-0ffae9ba1c224dfe8a50ca4d95f8de6a
出典データセット
uspto-grants-2011_05
特許番号
US07951794B2

関連ノート

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