Potassium Carbonate → HCID 21700327, compound

HRID 2229291Notes

Reaction equation

HRID 2229291 reaction equation
OC1C=C([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)C=C(S(C)(=O)=O)C=1OCCC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:32][O:31][C:23]1[CH:22]=[C:21]([CH:18]2[O:17][CH2:16][CH2:20][CH2:19]2)[CH:26]=[C:25]([O:27][CH3:28])[C:24]=1[O:29][CH3:30]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58753436HCID 58753436, compound

Product 1

HCID 21700327HCID 21700327, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Trans-2-(3-hydroxy-5-methylsulfonyl-4-propyloxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (242), 130 mg, 0.28 mmol) was dissolved in dry DMF (1.5 mL) and K2CO3 (58 Mg, 0.42 mmol) was added to it. Stirred, at room temperature under argon, for 30 min and a solution of 241, made above, in 1.0 mL of dry DMF was added. The resulting reaction mixture was stirred at 70° C. overnight. The reaction mixture was diluted with methylene chloride (25 mL) and washed with water (25 mL). The water layer was extracted once with 25 mL of methylene chloride. The combined methylene chloride extracts were dried over magnesium sulfate and concentrated in vacuo to obtain trans-2-13-methylsulfonyl-5-(4-phthalimido-but-2-ynyloxy)-4-propyloxyphenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran, 244, which was used without further purification. 1H-NMR (CDCl3) (5 7.85 (2H, dd, J=5.3, 3.2 Hz), 7.73 (2H, dd, J=5.3, 3.2 Hz), 7.55 (1 H, d, J=2.0 Hz), 7.32 (1 H, d, J=2.0 Hz), 6.62 (2H, s), 5.16-5.21 (2H, m), 4.77 (2H, s), 4.49 (2H, s), 4.11 (2H, t, J=6.8 Hz), 3.89 (6H, s), 3.84 (3H, s), 3.24 (3H, s), 2.41-2.46 (2H, m), 1.80-2.01 4H, m), 1.04 (3H, t, J=6.8 Hz).

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 70° C. overnight
  4. washwashed with water (25 mL)
  5. extractionThe water layer was extracted once with 25 mL of methylene chloride
  6. dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65972dfead5548fabebcbe58c1e7a64b
Source dataset
uspto-grants-2002_07
Patent number
US06420392B1

Reaction notes

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