Potassium Carbonate → HCID 86758175, compound

HRID 2186529Notes

Reaction equation

HRID 2186529 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@H:18]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)[O:19]2)[CH:5]=[C:6]([S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:7]=1[O:8][CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][CH2:43][CH2:44][N:45]1[C:49](=[O:50])[C:48]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:47]2[C:46]1=[O:55]>CC(C)=O>[C:46]1(=[O:55])[N:45]([CH2:44][CH2:43][CH2:42][O:1][C:2]2[CH:3]=[C:4]([C@H:18]3[CH2:22][CH2:21][C@H:20]([C:23]4[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=4)[O:19]3)[CH:5]=[C:6]([S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:7]=2[O:8][CH2:9][CH2:10][CH3:11])[C:49](=[O:50])[C:48]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:47]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 70156389HCID 70156389, compound

Product 1

HCID 86758175HCID 86758175, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (±)-trans-2-(3-hydroxy-4-propoxy-5-propylsulfonylphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (2.80 g, 5.66 mol) in acetone (40 ml) were added potassium carbonate (1.01 g, 7.36 mol) and N-(3-bromopropyl) pthalimide (2.06 g, 8.50 mmol). The reaction mixture was refluxed for 16 h. The reaction mixture was cooled to room temperature and acetone was removed, water was added and extracted with ethyl acetate (120 ml), dried (Na2SO4), filtered and concentrated. The crude product was purified on silica gel column using Ethyl acetate:light petroleum (2:5) to give (±)-trans-2-[3-(3-pthalimidopropoxy)-4-propoxy-5-propylsulfonyl phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran as solid (3.71 g, 94%). TLC: Ethyl acetate:light petroleum (2:1), Rf=0.5 ; m.p. 195-196° C. 1H NMR (CDCl3, 200 MHz): δ 1.05 (t, J=7.14 Hz, 3H), 1.08 (t, J=6.66 Hz, 3H), 1.68-2.06 (m, 6H), 2.2-2.3 (m, 2H), 2.4-2.55 (m, 2H), 3.35 (m, 2H), 3.83 (s, 3H), 3.9 (s, 6H), 3.95 (t, J=6.6 Hz, 2H), 4.15 (t, J=6.13 Hz, 4H), 5.2 (m, 2H), 6.58 (s, 2H), 7.23 (d, J=1.5 Hz, 1H), 7.45 (d, J=1.51 Hz, 1H), 7.7 (m, 2H), 7.85 (m, 2H); IR (neat): 3010, 2975, 1775, 1715, 1600, 1490, 1380 cm−1 FAB Mass: 681(M+); HRMS: calculated. 681.260769; found. 681.265005.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customacetone was removed
  3. additionwater was added
  4. extractionextracted with ethyl acetate (120 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified on silica gel column

Sources & evidence

ORD record
ord-cd543d8aab134a6db8312f2ac278bcec
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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