HCID 58753189, compound → HCID 21700327, compound

HRID 2186528Notes

Reaction equation

HRID 2186528 reaction equation
C(OC1C=C([C@H:25]2[CH2:29][CH2:28][C@H:27]([C:30]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=3)[O:26]2)C=C(S(CCC)(=O)=O)C=1OCCC)C1C=CC=CC=1>C(OCC)(=O)C>[CH3:41][O:40][C:32]1[CH:31]=[C:30]([CH:27]2[CH2:28][CH2:29][CH2:25][O:26]2)[CH:35]=[C:34]([O:36][CH3:37])[C:33]=1[O:38][CH3:39]

Participants

3

Reactant 1

HCID 58753189HCID 58753189, compound

Product 1

HCID 21700327HCID 21700327, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (±)-trans-2-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (6.35 g, 10.87 mol) in ethyl acetate (50 ml) was added 10% pd/c (0.80 g). The reaction mixture was stirred at room temperature under balloon pressure for 2 h. The Pd/C was filtered through celite and washed with ethyl acetate (80 ml). The filtrate was concentrated and the crude product was purified through silica gel column using Ethyl acetate:light petroleum (1:3) to give (±)-trans-2-(3-hydroxy-4-propoxy-5-propylsulfonylphenyl)-5-(3,4,5-trimethoxyphenyl tetrahydrofuran as a solid (3.30 g, 61%). TLC: Ethyl acetate:light petroleum (3:2), Rf=0.5 ; m.p. 115-117° C.; 1H NMR (CDCl3, 200 MHz): δ 0.95 (t, J=7.72 Hz, 3H), 1.0 (t, J=6.81 Hz, 3H), 1.6-1.95 (m, 6H), 2.3-2.42 (m, 2H), 3.25 (m, 2H), 3.75 (s, 3H), 3.80 (s, 6H), 4.03 (t, J=6.12 Hz, 2H), 5.0-5.13 (m, 2H), 6.28 (s, 1H), 6.5 (s, 2H), 7.18 (d, J=1.54 Hz, 1H), 7.34 (d, J=1.54 Hz, 1H); IR (neat): 3400, 2975, 2945, 2860, 1725, 1540, 1490, 1440 cm−1. FAB Mass: 495 (M+), HRMS:calculated 0.495.205265; found. 495.207215.

Workup

  1. filtrationThe Pd/C was filtered through celite
  2. washwashed with ethyl acetate (80 ml)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified through silica gel column

Sources & evidence

ORD record
ord-62922a7d1a374bfaba99acb49ef1a09d
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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