2-[3-(2-Oxopropylsufonyl)-4-n-propoxy-5-benzyloxy-phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran → 2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy 5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydro-furan
Reaction equation
[O:1]=[C:2]([CH3:42])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([CH:25]2[CH2:29][CH2:28][CH: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(O)(=O)C.C(OCC)(=O)C.[Pd]>[O:1]=[C:2]([CH3:42])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([CH:25]2[CH2:29][CH2:28][CH: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
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 1.2 g of 2-[3-(2-oxopropylsufonyl)-4-n-propoxy-5-benzyloxy- phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran, 400 mg 10% Pd/C, 1-2 drops of acetic acid in 100 mL of ethyl acetate was stirred under H2 at 40 psi for 45 minutes. The reaction mixture was filtered over a bed of celite and evaporated in vacuo to yield the title compound: NMR(200 MHz, CDCl3) δ 1.10 (t, CH2CH2CH3), 1.92 (m, CH2CH2CH3), 1.9-2.6 (m, 3-CH2 & 4-CH2), 2.40 (s, CH3C(O)CH2), 3.86 (s, OCH3), 3.90 (s, 2 OCH3), 4.12 (t, OCH2CH2CH3), 4.42 (s, CH3C(O)CH2), 5.10-5.28 (m, 2-CH & 5-CH), 6.64 (s, 5-ArH), 7.35 & 7.47(2 d, 2-ArH).
Workup
- filtrationThe reaction mixture was filtered over a bed of celite
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-14763611064843f8adcc3d65dafa9b9a
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977146
Reaction notes
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