Ethyl Acetate → HCID 21876949, compound

HRID 2121052Notes

Reaction equation

HRID 2121052 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[S:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=3)[S:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21876833HCID 21876833, compoundHCID 43835034Tin dichloride dihydrate

Product 1

HCID 21876949HCID 21876949, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(4-cyclopentyloxythien-2-ylmethyl)-nitrobenzene (1.28 g, 4.2 mmol) in absolute ethanol (34 mL) was added tin dichloride hydrate (4.76 g, 21.2 mmol) at 20-25° C. under nitrogen. The mixture was heated at 75° C. for 2.5 hours and cooled to 0-5° C. Saturated sodium bicarbonate was added to pH 8. Ethyl acetate was added and the mixture was filtered. The layers were separated, and the aqueous phase was extracted with additional ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography (silica, hexane/ethylacetate) gave 4-(4-cyclopentyloxythien-2-ylmethyl)-phenylamine (0.47 g, 41%) as a pale yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.03 (d, J=8.5 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 6.41 (m, 1H), 5.96 (d, J=1.7 Hz, 1H, 4.58 (quintet, J=4.3 Hz, 1H), 3.91 (s, 2H), 3.59 (bs, 2H), 1.67-1.88 (m, 6H), 1.46-1.67 (m, 2N).

Workup

  1. temperaturecooled to 0-5° C
  2. filtrationthe mixture was filtered
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with additional ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customPurification by flash chromatography (silica, hexane/ethylacetate)

Sources & evidence

ORD record
ord-afe0fa8877754250b5ea52a2bf3cf8f3
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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