Tetrahydrofuran → HCID 18798682, compound

HRID 356458Notes

Reaction equation

HRID 356458 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17](=[O:34])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:21]=2)[CH:12]=[CH:13][CH:14]=1)[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:22]1[CH:21]=[C:20]([CH2:19][CH2:18][C:17](=[O:34])[CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24414Barium SulfateHCID 54567841HCID 54567841, compoundHCID 131709961Jones' reagent

Product 1

HCID 18798682HCID 18798682, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Hydrogenation of 5.20 g (42.6 mmol) of 1,5-bis-(3-benzyloxy-phenyl)-penta-1,4-dien-3-one prepared in Example E was effected as described in General Method 3 using 0.5 g 5% Pd over BaSO4 and 150 mL of THF under hydrogen atmosphere. The product contained both ketone and alcohol, so the mixture was dissolved in acetone (approximately 200 mL) and treated with 5 mL of 8.0N Jones reagent. The mixture was stirred for 2 hours at room temperature, treated with isopropanol, and filtered through Celite. The filtrate was concentrated, and the residue was triturated with 1:1 hexane:EtOAc to give the title compound. 1H NMR (CDCl3) δ 2.69 (m, 4 H), 2.85 (m, 4 H), 5.03 (s, 4 H), 6.58-6.81 (m, 6 H), 7.18 (m, 2 H), 7.28-7.41 (m, 10 H).

Workup

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

Sources & evidence

ORD record
ord-4f860258c3b3450b99cbe1482068a3d0
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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