Tetramethyltin → 5-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one

HRID 1502037Notes

Reaction equation

HRID 1502037 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]=1

Participants

8

Reactant 4

HCID 11661TetramethyltinHCID 11776TriphenylphosphineHCID 13387N-methyl-2-pyrrolidoneHCID 666438705-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one

Product 1

HCID 666440355-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 25517Ammonium ChlorideSolvent

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 (1.00 g, 3.95 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). Then the mixture was heated for another 10 min, after which 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 room temperature, 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 preparative HPLC to give 5-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one.

Workup

  1. customThe mixture was purged with N2
  2. temperatureThen the mixture was heated for another 10 min
  3. temperaturewas heated to 120° C. for 2 h
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with EtOAc (3×200 mL)
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-58c3f7782780425ebc640f7fdcfbd0e5
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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