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

HRID 277296

반응식

HRID 277296 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7acf2b799cac4431a234b209a1175f8a
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355683B1

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