Sodium Bicarbonate → HCID 58400514, compound
Reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@@H:5]([CH:7]([OH:10])[CH:8]=[CH2:9])[CH2:4][O:3]1.C(=O)([O-])O.[Na+].C(O[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1Br)(=O)C>CN(C=O)C.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:27][C:24]1[CH:23]=[C:22]2[C:21](=[CH:26][CH:25]=1)[O:10][CH:7]([C@H:5]1[CH2:4][O:3][C:2]([CH3:11])([CH3:1])[O:6]1)[CH:8]=[CH:9]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 120 °C
Procedure
1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (0.3 g, 1.90 mmol), sodium hydrogen carbonate (0.22 g, 2.58 mmol), 2-bromo-4-fluorophenyl acetate (0.3 g, 1.29 mmol), palladium acetate (14 mg, 0.06 mmol) and CYTOP 216, 2,4,6 trioxy 1,3,5,7 tetramethyl 8 phosphaadamantane (19 mg, 0.06 mmol) were suspended in DMF (5 ml) under nitrogen. The reaction mixture was stirred at 120° C. for 19 h, cooled to 25° C. and then diluted with ethyl acetate (20 ml) and demi water (20 ml). The phases were separated and the organic layer dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to dryness. The crude reaction mixture was then purified by flash chromatography on silica (heptane:ethyl acetate 9:1) and 6-fluoro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene was isolated as a pale yellow oil (60 mg, 19% yield).
Workup
- temperaturecooled to 25° C.
- customThe phases were separated
- dry with materialthe organic layer dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum to dryness
- customThe crude reaction mixture
- customwas then purified by flash chromatography on silica (heptane:ethyl acetate 9:1)
Sources & evidence
- ORD record
- ord-92c344ab9cce480196ca1127fced1662
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07999124B2
Reaction notes
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