Sodium hydride → HCID 69968403, compound

HRID 2289118Notes

Reaction equation

HRID 2289118 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][N:6]=1)[CH3:4].CS(O[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][CH:28]=1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:17][CH:24]([CH3:23])[CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][CH:28]=3)=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][N:6]=1)[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 18701959HCID 18701959, compoundHCID 135723525HCID 135723525, compound

Product 1

HCID 69968403HCID 69968403, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of sodium hydride (15 mg, 0.36 mmole) in DMF (1.5 mL) was treated with 3-ethyl-6-hydroxy-7-propylbenz-[4,5]-isoxazole (68 mg, 0.33 mmole) and the mixture stirred at room temperature for 10 minutes under a nitrogen atmosphere. A solution of methyl 4-(4-methansulfonyloxybutyl)phenylacetate (100 mg, 0.33 mmole) in DMF (0.5 mL) was added and the mixture stirred at 80° C. for 5 hours. The cooled reaction mix was dissolved in ethyl acetate and washed with water (twice), brine, dried over magnesium sulfate and concentrated in vacuo to an oil. The crude product was purified by thin layer chromatography on silica gel eluting with hexane:ethyl acetate (4:1) to give the title compound (80 mg) as an oil. NMR (CDCl3): δ 0.97 (t, 3H); 1.44 (t, 3H); 1.71 (m, 2H); 1.87 (m, 4H); 2.71 (t, 2H); 2.88 (t, 2H); 2.97 (q, 2H); 3.62 (s, 2H); 3.71 (s, 3H); 6.89 (d, 1H); 7.18 (d, 2H); 7.22 (d, 2H); 7.39 (d, 1H).

Workup

  1. stirringthe mixture stirred at 80° C. for 5 hours
  2. customThe cooled reaction
  3. additionmix
  4. washwashed with water (twice), brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo to an oil
  7. customThe crude product was purified by thin layer chromatography on silica gel eluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-acb4083e649e48a4a1a073cfb952f449
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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