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

HRID 1186950Notes

Reaction equation

HRID 1186950 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 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 cooled 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 prep-HPLC to give 5-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one.

Workup

  1. customThe mixture was purged with N2
  2. temperatureAfter the mixture was heated for another 10 min
  3. temperaturewas heated to 120° C. for 2 h
  4. temperatureAfter cooled 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 prep-HPLC

Sources & evidence

ORD record
ord-d12525b4de434726b887d87badc1732a
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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