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

Diethyl Ether → 2(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

HRID 1019193
Notes
Print preview

Reaction equation

HRID 1019193 reaction equation
I[C:2]1[C:3](=[O:15])[O:4][CH2:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C1C=CC=CC=1.[OH-].[Na+].C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[C:16]1([C:2]2[C:3](=[O:15])[O:4][CH2:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 11773TriphenylarsineHCID 66827Phenylboronic AcidHCID 121505903-iodo-4-(4-(methylthio)phenyl)-2-(5H)-furanone

Product 1

HCID 110442352(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

Reagents, catalysts & solvents 3

HCID 498840
Bis(benzonitrile)palladium chloride
Catalyst
HCID 241BenzeneSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4 g of the product of Step 3, 3.7 g of PhB(OH)2, 0.4 g of Ph3As, 0.4 g of PdCl2(PhCN)2 in 100 ml of benzene and 15 ml of 2N NaOH is refluxed for 6 h. Ether(200 ml) is then added and the mixture is washed with 100 ml of saturated NaHCO3. The organic layer is dried over MgSO4 and concentrated. The residue is purified by flash chromatography on silica gel eluted with 4:1 hexane/EtOAc to give the tide compound.

Workup

  1. temperatureis refluxed for 6 h
  2. washthe mixture is washed with 100 ml of saturated NaHCO3
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluted with 4:1 hexane/EtOAc
  7. customto give the tide compound

Sources & evidence

ORD record
ord-f54cca4d6bba48b5b1bed8a4c7162755
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06486194B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes