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

HRID 356456Notes

Reaction equation

HRID 356456 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:34])[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)=[CH:22][CH:21]=2)=[CH:11][CH:10]=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:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][C:17](=[O:34])[CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)=[CH:21][CH:22]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24414Barium SulfateHCID 4714751,5-Bis-(4-benzyloxy-phenyl)-penta-1,4-dien-3-oneHCID 131709961Jones' reagent

Product 1

HCID 541582871,5-Bis (4-benzyloxy-phenyl)-pentan-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Hydrogenation of 24.4 g (54.7 mmol) of 1,5-bis-(4-benzyloxy-phenyl)-penta-1,4-dien-3-one prepared in Example A was effected as described in General Method 3 using 1.0 g 5% Pd over BaSO4 and 1000 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 10 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 to afford the title ketone. 1H NMR (CDCl3) δ 2.67 (m, 4 H), 2.82 (m, 4 H), 5.03 (s, 4 H), 6.88 (d, 4 H), 7.05 (d, 4 H), 7.30-7.43 (m, 10 H).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b98ca167b6dc440ba1ccb5d8dd220b7d
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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