Sodium Hydroxide → 1,3-Bis(m-carboxyphenyl)-1-propanol

HRID 277296

反応式

HRID 277296 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+]>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:20]([C:16]1[CH:15]=[C:14]([CH:12]([OH:13])[CH2:11][CH2:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[CH:19]=[CH:18][CH:17]=1)([OH:22])=[O:21]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 538375063,3'-Dicarboxychalcone

生成物 1

HCID 226017891,3-Bis(m-carboxyphenyl)-1-propanol

試薬・触媒・溶媒 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)触媒HCID 702Ethanol溶媒

実験手順

3,3′-Dicarboxychalcone (Example 4, step 2) (430 mg, 1.45 mmol) in ethanol (10 mL) containing aqueous NaOH (1 M, 2.90 mmol) was hydrogenated at 45 psi for 48 hours in the presence of Wilkinson's catalyst (67 mg, 0.07 mmol). The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in methanol (10 mL) and treated with NaBH4 (220 mg, 5.8 mmol) at rt. The reaction mixture was stirred for 16 hours at rt, quenched with the cautious addition of saturated aqueous NH4Cl and partitioned between EtOAc (50 mL) and aqueous HCl (1 M, 50 mL). The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give 1,3-bis (m-carboxyphenyl)-1-propanol as a viscous oil. MS (APCI) m/z 299 (M+−1, 100%). 1H NMR (200 MHz, CDCl3); δ1.95-2.10, m, 2H; 2.68-2.83, m, 2H; 4.62-4.78, m, 1H; 7.03-7.60, m, 4H; 7.75-8.03, m, 4H.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol (10 mL)
  4. customquenched with the cautious addition of saturated aqueous NH4Cl
  5. custompartitioned between EtOAc (50 mL) and aqueous HCl (1 M, 50 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7acf2b799cac4431a234b209a1175f8a
出典データセット
uspto-grants-2002_03
特許番号
US06355683B1

関連ノート

読み込み中…