Sodium Carbonate → 4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].FC(F)(F)S(O[C:19]1[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH:20]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:23]1[C:22]2([CH2:27][CH2:28][C:19]([C:7]3[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=3)=[CH:20][CH2:21]2)[O:26][CH2:25][CH2:24]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-carboxyphenylboronic acid (0.69 g, 3.53 mmol) and 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (1.02 g, 3.53 mmol) in 14 mL of DMF were added 7 mL of 2 N aqueous solution of Na2CO3, triphenylphosphine (159 mg, 0.61 mmol), and tris(dibenzylideneacetone)dipalladium(0) (68 mg, 74.2 μmol). After stirring at 80° C. for 3 h and then at rt for 16 h, the mixture was concentrated and partitioned between 100 mL of Et2O and 150 mL of H2O. The aqueous layer was separated and acidified to pH ˜2-3 using concentrated HCl, and extracted with CH2Cl2 (2×100 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The residue was re-crystallized from 10 mL of EtOAc to give 353 mg (38%) of the title compound.
Workup
- waitat rt for 16 h
- concentrationthe mixture was concentrated
- custompartitioned between 100 mL of Et2O and 150 mL of H2O
- customThe aqueous layer was separated
- extractionextracted with CH2Cl2 (2×100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was re-crystallized from 10 mL of EtOAc
Sources & evidence
- ORD record
- ord-0e489130b3e44dfe81078b3cabfffdd1
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659294B2
Reaction notes
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