HCID 15078315, compound → HCID 15078317, compound

HRID 1110837Notes

Reaction equation

HRID 1110837 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([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)[CH:10]=[C:11]([O:17]CC2C=CC=CC=2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]>C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:25]2[CH2:29][CH2:28][C@H:27]([C:30]3[CH:31]=[C:32]([O:40][CH3:41])[C:33]([O:38][CH3:39])=[C:34]([O:36][CH3:37])[CH:35]=3)[O:26]2)[CH:10]=[C:11]([OH:17])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

4

Reactant 1

HCID 15078315HCID 15078315, compound

Product 1

HCID 15078317HCID 15078317, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-2-[3-(2-hydroxyethylsulfonyl)-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetra-hydrofuran (440 mg) in ethyl acetate (6 mL) was hydrogenated over 10% palladium on charcoal (120 mg) at 45 psi for 1 h. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were evaporated to give the title compound Rf 0.1 (hexane-ethyl acetate; 1:1, v/v); NMR (CDCl3) δ 1.07 (t, CH2CH2CH3), 3.60 (q, SO2CH2), 3.95 (q, SO2CH2CH2), 3.84 (s, OCH3), 3.88 (s, 2 OCH3), 4.11 (t, CH2CH2CH3), 5.13-5.25 (m, H-2 & H-5), 6.61 (s, 2 H, C5ArH), 7.32 & 7.49 (2 d, J=2.0 Hz, C2ArH).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-fc58cd73cdce4f95bca077b5f05741f6
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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