Methanol → HCID 22731288, compound

HRID 2085576Notes

Reaction equation

HRID 2085576 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]2[CH:7]=[C:8](B(O)O)[CH:9]=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]=2[O:4][CH2:3]1.CO.[C:21]1([CH3:27])C=CC=[CH:23][CH:22]=1.C(=O)([O-])[O-:29].[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([CH3:18])[C:6]2[CH:7]=[C:8](/[C:21](/[CH3:27])=[CH:22]\[CH2:23][OH:29])[CH:9]=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]=2[O:4][CH2:3]1

Participants

9

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 22731304HCID 22731304, compound2×

Product 1

HCID 22731288HCID 22731288, compound

Reagents, catalysts & solvents 4

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

Procedure

Following General Procedure B and using 3,3-dimethyl-7-t-butyl-2,3-dihydro-benzofuran-5-boronic acid (Intermediate 25, 0.57 g, 2.3 mmol), 3-iodo-but-2 (Z)-ene-ol (0.4 g, 2 mmol), methanol (7.5 mL), toluene (15 mL), water (2 mL), sodium carbonate (0.5 g, 4.9 mmol) and tetrakis(triphenylphosphine)palladium(0)(60 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 (0.47 g, 57% over two steps).

Sources & evidence

ORD record
ord-5f250d919f8148efb19de55b913b3a2b
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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