trans-2-(5-Propylsulfonyl-4-benzyloxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran → trans-2-(5-propylsulfonyl-4-Hydroxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran

HRID 1196707Notes

Reaction equation

HRID 1196707 reaction equation
[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:21][CH3:22])[C:12]=1[O:13]CC1C=CC=CC=1)(=[O:6])=[O:5])[CH2:2][CH3:3]>C(OCC)(=O)C>[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:21][CH3:22])[C:12]=1[OH:13])(=[O:6])=[O:5])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 67907048trans-2-(5-Propylsulfonyl-4-benzyloxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran

Product 1

HCID 67906973trans-2-(5-propylsulfonyl-4-Hydroxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-2-(3-n-propylsulfonyl-4-benzyloxy-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (5.0 g) in ethyl acetate (100 mL) was hydrogenated over 10% palladium-over-charcoal (250 mg) for 1 h. The catalyst was filtered off and the filtrate was concentrated to a crystalline mass. Recrystallization from ethyl ether gave pure product: mp 168°-169° C.; NMR (CDCl3) δ 1.0 (t, CH2CH2CH3), 1.7 (m, CH2CH2CH3), 2.0 & 2.49 (2 m, H-3 & H-4), 3.4 (m, CH2CH2CH3), 3.84, 3.89 & 3.93 (3 s, 4 OCH3), 5.20 (m, H-2 & H-5), 6.62 (s, C5ArH), 7.24 & 7.47 (2 d, J=1.5 Hz, C2ArH).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to a crystalline mass
  3. customRecrystallization from ethyl ether
  4. customgave pure product

Sources & evidence

ORD record
ord-d36f978211ed43ce839b79ed3932c65a
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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