Methanol → HCID 69887938, compound

HRID 2085599Notes

Reaction equation

HRID 2085599 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.CO.[C:17]1([CH3:23])C=CC=C[CH:18]=1.C(=O)([O-])[O-:25].[Na+].[Na+]>CCCCCC.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(OCC)(=O)C.O>[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[C:8](/[CH:18]=[CH:17]\[CH2:23][OH:25])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

9

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 22731317HCID 22731317, compound2×

Product 1

HCID 69887938HCID 69887938, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure B and using 3,3-dimethyl-2,3-dihydro-benzofuran-5-boronic acid (Intermediate 3, crude, 10 mmol), 3-iodo-prop-2 (Z)-ene-ol (Intermediate 69, 1.35 g, 7.29 mmol), methanol (20 mL), toluene (40 mL), water (10 mL), sodium carbonate (1.58 g, 15 mmol) and tetrakis(triphenylphosphine)palladium(0)(100 mg), followed by flash column chromatography over silica gel (230-400 mesh) using 15% ethyl acetate in hexane as the eluent the title compound was obtained (0.16 g, 8%).

Sources & evidence

ORD record
ord-093671c42d9743aba4f19f75124e9b59
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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