p-Toluenesulfonic acid → HCID 18367277, compound

HRID 1741404Notes

Reaction equation

HRID 1741404 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[C:14]1([C:20]2[N:21]=[C:22]([CH:31]([NH2:33])[CH3:32])[O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:14]1([C:20]2[N:21]=[C:22]([CH:31]([NH:33][CH:8]3[C:9]4[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=4)[CH2:5][CH2:6][CH2:7]3)[CH3:32])[O:23][C:24]=2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 366205-MethoxytetraloneHCID 541979HCID 541979, compound

Product 1

HCID 18367277HCID 18367277, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene (0.67 g), 1-(4,5-diphenyloxazol-2-yl)ethylamine (0.98 g) and p-toluenesulfonic acid (catalytic amount) in toluene (30 ml) was refluxed for 7 hours with Dean-stark equipment. The solution was evaporated in vacuo and methanol (MeOH) (10 ml) was added to the residue. To the MeOH solution, NaBH4 (0.21 g) was added at 0° C. After being stirred for 2 hours at room temperature, the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine. The dried solvent was evaporated in vacuo, and the residue was purified by chromatography on silica gel to give 1-[1-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-methoxynaphthalene (0.73 g). MS (m/z): 425 (M+ +1) NMR (CDCl3, δ): 1.60 (3H, d, J=6.8 Hz), 1.60-2.08 (6H, m), 2.42-2.86 (2H, m), 3.80 (1.5H, s), 3.81 (0.5H, q, J=6.8 Hz), 3.82 (1.5H, s), 3.90 (0.5H, m), 4.29 (0.5H, q, J=6.8 Hz), 4.77 (0.5H, m), 6.73 (1H, m), 7.00-7.20 (2H, m), 7.33-7.39 (6H, m), 7.57-7.68 (4H, m)

Workup

  1. customThe solution was evaporated in vacuo and methanol (MeOH) (10 ml)
  2. additionwas added to the residue
  3. additionTo the MeOH solution, NaBH4 (0.21 g) was added at 0° C
  4. customthe solution was evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. customThe dried solvent was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-15f37dacb016452cba8b2c10ec8f4e70
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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