Tetrahydrofuran → 1,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-pentan-3-one

HRID 356457Notes

Reaction equation

HRID 356457 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:36])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:22]([O:34][CH3:35])[CH:21]=2)=[CH:11][C:10]=1[O:37][CH3:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S([O-])(=O)=O.[Ba+2].C1COCC1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.[Pd].C(O)(C)C>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][C:17](=[O:36])[CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([O:37][CH3:38])[CH:11]=2)=[CH:21][C:22]=1[O:34][CH3:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24414Barium SulfateHCID 537669791,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-penta-1,4-dien-3-oneHCID 131709961Jones' reagent

Product 1

HCID 187986361,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-pentan-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Hydrogenation of 21.5 g (42.6 mmol) of 1,5-bis-(4-benzyloxy-3-methoxy-phenyl)-penta-1,4-dien-3-one prepared in Example D was effected as described in General Method 3 using 1.0 g 5% Pd over BaSO4 and 600 mL of THF under hydrogen atmosphere. The product contained both ketone and alcohol. Therefore, the mixture was dissolved in acetone (approximately 500 mL), treated with 20 mL of 8.0N Jones reagent, and stirred overnight at room temperature. Isopropanol was added, and the mixture was filtered through Celite. The filtrate was concentrated, and the residue was triturated with 1:1 hexane:EtOAc to give the title compound. 1H NMR (DMSO-d6) δ 2.71 (m, 8 H), 3.74 (s, 6 H), 5.02 (s, 4 H), 6.66 (m, 2 H), 6.82 (br s, 2 H), 6.87 (m, 2 H), 7.29-7.43 (m, 10 H).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was triturated with 1:1 hexane

Sources & evidence

ORD record
ord-e58642045dff432ea8bd34052b6fb122
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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