Dimethylformamide → HCID 58753263, compound

HRID 1599489Notes

Reaction equation

HRID 1599489 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([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)[CH:5]=[C:6]([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]=1[O:8][CH2:9][CH2:10][CH3:11].[C:33]([O-:36])([O-])=O.[K+].[K+].[CH3:39][N:40]([CH:42]=[O:43])C>C(Cl)Cl>[CH3:15][S:12]([C:6]1[CH:5]=[C:4]([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)[O:17]2)[CH:3]=[C:2]([O:1][CH2:11][C:10]#[C:9][CH2:39][N:40]2[C:42](=[O:43])[C:7]3=[CH:6][CH:5]=[CH:4][CH:3]=[C:2]3[C:33]2=[O:36])[C:7]=1[O:8][CH2:9][CH2:10][CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 58753436HCID 58753436, compound

Product 1

HCID 58753263HCID 58753263, compound

Reagents, catalysts & solvents 1

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-[3-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) δ7.85 (2H, dd, J=5.3, 3.2 Hz), 7.73 (2H, dd, J=5.3, 3.2 Hz), 7.55 (1H, d, J=2.0 Hz), 7.32 (1H, 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-b2dd0c67e1c0468f84c303e02961c5bc
Source dataset
uspto-grants-1998_04
Patent number
US05741809

Reaction notes

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