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 1085634Notes

Reaction equation

HRID 1085634 reaction equation
[CH2:1]([S:4]([C:7]1[C:8]([O:32]CC2C=CC=CC=2)=[C:9]([O:30][CH3:31])[CH:10]=[C:11]([C@H:13]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)[O:14]2)[CH:12]=1)(=[O:6])=[O:5])[CH2:2][CH3:3]>C(OCC)(=O)C>[CH2:1]([S:4]([C:7]1[C:8]([OH:32])=[C:9]([O:30][CH3:31])[CH:10]=[C:11]([C@H:13]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)[O:14]2)[CH:12]=1)(=[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-(5-propylsulfonyl-4-benzyloxy-3-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-4d011b1467d843b5b247a88fbccc8879
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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