HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1003811
Notes
Print preview

Reaction equation

HRID 1003811 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938
Palladium
Catalyst
HCID 180AcetoneSolvent
HCID 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-9378d91ba79b432f82f9d42ce0f98146
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06046355

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes