Water → 5H-Furo[3,2-b]pyran-5-one, hexahydro-2-phenyl-3a-(1-phenylethenyl)-

HRID 1354582Notes

Reaction equation

[C:1]1([CH:7]2[O:11][CH:10]([CH:12]([CH3:16])C(O)=O)[C:9](=[C:17]=[CH2:18])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]([O-:22])([O-])=[O:20].[K+].[K+].[C:25]1(I)[CH:30]=[CH:29]C=[CH:27][CH:26]=1.O.[CH3:33]N(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:17]([C:18]4[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=4)=[CH2:33])([O:22][C:19](=[O:20])[CH2:16][CH2:12]3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(5-phenyl-3-vinylidene-tetrahydro-furan-2-yl)propionic acid (60 mg, 0.25 mmol), Pd(PPh3)4 (29 mg, 0.025 mmol), K2CO3 (170 mg, 1.23 mmol) were dissolved in 6 mL of dimethylformamide, followed by addition of PhI (138 μL, 1.23 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 (52 mg, 67%).

Workup

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

Sources & evidence

ORD record: ord-64548612fde7458794d98b3f9ccecff0
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223874B2

Reaction notes

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