Water → HCID 21106111, compound

HRID 1354579Notes

Reaction equation

HRID 1354579 reaction equation
[C:1]1([CH:7]2[O:11][CH:10]([CH2:12][C:13]([OH:15])=[O:14])[C:9](=[C:16]=[CH2:17])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:24]1(I)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([CH:7]2[O:11][CH:10]3[C:9]([C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH2:17])([O:14][C:13](=[O:15])[CH2:12]3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 21106109HCID 21106109, compound

Product 1

HCID 21106111HCID 21106111, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

(5-phenyl-3-vinylidene-tetrahydro-furan-2-yl)acetic acid (32 mg, 0.12 mmol), Pd(PPh3)4 (14 mg, 0.012 mmol) and K2CO3 (84 mg, 0.61 mmol) were dissolved in 3 mL of dimethylformamide, followed by addition of PhI (68 μL, 0.61 mmol). The solution was stirred for 4 hours at 85° C. When the reaction was completed, H2O was added and the solution was stirred for 5 minutes. The mixture was diluted with ethyl acetate, washed with H2O and NaCl. Organic layer was separated and dried with anhydride MgSO4. Solvent was removed under reduced pressure, and the remnant was purified through silica gel tube chromatography (EtOAc:n-Hexane=1:15, v/v), thus providing products (26 mg, 62%).

Workup

  1. stirringthe solution was stirred for 5 minutes
  2. washwashed with H2O and NaCl
  3. customOrganic layer was separated
  4. dry with materialdried with anhydride MgSO4
  5. customSolvent was removed under reduced pressure
  6. customthe remnant was purified through silica gel tube chromatography (EtOAc

Sources & evidence

ORD record
ord-bb6e7ec3f3c449d69e94a7ce933ce469
Source dataset
uspto-grants-2007_05
Patent number
US07223874B2

Reaction notes

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