Ethanol → HCID 18974013, compound

HRID 2394999Notes

Reaction equation

HRID 2394999 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+].[CH2:41]([OH:43])[CH3:42]>>[CH3:42][C:41]([NH:1][C:4]1[CH:5]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)[CH:7]=[CH:8][CH:9]=1)=[O:43]

Participants

5

Reactant 4

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18973912HCID 18973912, compound

Product 1

HCID 18974013HCID 18974013, compound

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-[3-(2-(3-nitrophenylmethyloxy)-phenyl)propyl]benzoate (0.25 g), tin (II) chloride dihydrate (0.7 g) in ethanol (10 ml) was heated at 70° C. for 45 minutes, cooled and poured onto ice. The pH of the solution was adjusted to 8 with sodium bicarbonate and extracted with ethyl acetate (2×50 ml). The combined organics were washed with brine (50 ml), dried (magnesium sulphate), filtered and evaporated. The residue was purified by subjecting to chromatography on silica gel using ethyl acetate hexane (1:9) as eluant. There was thus obtained methyl 4-[3-(2-(3-aminophenylmethyloxy)phenyl)propyl]benzoate (185 mg). b: - Methyl 4-[3-(2-(3-methylcarbonylaminophenylmethyloxy)-phenyl) propyl]benzoate was prepared from methyl 4-[3-(2-(3-amino-phenylmethyloxy)phenyl)propyl]benzoate (preparation described in note a) as follows:

Workup

  1. temperaturecooled
  2. additionpoured onto ice
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organics were washed with brine (50 ml)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified
  9. custompreparation

Sources & evidence

ORD record
ord-ebf7c261a4bc4f0cb72b5c550b8f828d
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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