Tetramethyltin → 5-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13](I)=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[CH:15]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN1C(=O)CCC1.[Sn](C)(C)(C)C>[NH4+].[Cl-].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].[Cu]I>[OH:1][CH2:2][CH2:3][C:4]1[C:13]([CH3:15])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a flask charged with 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one (6.00 g, 19.7 mmol) and a stir bar was added Pd2(dba)3 (452 mg, 0.493 mmol), PPh3 (1 g, 4 mmol) and NMP (50 mL). The mixture was purged with N2 and heated to 50° C. for 10 min, followed by addition of CuI (375 mg, 1.97 mmol). After the mixture was heated for another 10 min, Sn(CH3)4 (5.30 g, 29.6 mmol) was added into the reaction, and it was heated to 120° C. for 2 h. After cooling to RT, the mixture was diluted with saturated NH4Cl (200 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by prep-HPLC to give the title compound.
Workup
- customThe mixture was purged with N2
- temperatureAfter the mixture was heated for another 10 min
- temperaturewas heated to 120° C. for 2 h
- temperatureAfter cooling to RT
- extractionextracted with EtOAc (3×200 mL)
- washThe combined organic layers were washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by prep-HPLC
Sources & evidence
- ORD record
- ord-401f3fd6438842ec94e5f2e327a53171
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999991B2
Reaction notes
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