4-Formylbenzoic acid → 4-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

HRID 24586

反応式

HRID 24586 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16](=[O:18])[CH3:17])=[CH:13][CH:14]=2)[C:9]([CH3:20])([CH3:19])[CH2:8][CH:7]=1.[C:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)([OH:23])=[O:22].[OH-].[Na+]>CO>[O:18]=[C:16]([C:12]1[CH:13]=[CH:14][C:15]2[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH2:8][C:9]([CH3:20])([CH3:19])[C:10]=2[CH:11]=1)[CH:17]=[CH:28][C:27]1[CH:30]=[CH:31][C:24]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1

参加物

5

反応物 3

HCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 225715413,4-Dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene

生成物 1

HCID 545281504-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 62.6-mg (0.222 mmol) 3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene (Compound D33) in 4.0 mL of MeOH were added 33.4 mg (0.222 mmol) of 4-carboxy benzaldehyde, and 240.0 mg (6.00 mmol; 2.0 mL of 3M aqueous NaOH). The resulting solution was stirred at room temperature for 12 h, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer washed with H2O, and saturated aqueous NaCl, before being dried over Na2SO4. Removal of the solvents under reduced pressure gave the title compound as a pale green solid after recrystallization from EtOH.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residual oil dissolved in EtOAc
  3. additionThe solution was treated with 10% HCl
  4. washthe organic layer washed with H2O, and saturated aqueous NaCl
  5. dry with materialbefore being dried over Na2SO4
  6. customRemoval of the solvents under reduced pressure

出典と根拠

ORDレコード
ord-1313fb2a46c74e41ba43a2712ec20dc4
出典データセット
uspto-grants-2005_02
特許番号
US06855832B2

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