Ethyl Acetate → HCID 66646404, compound

HRID 1848425Notes

Reaction equation

HRID 1848425 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH2:13][OH:14].[CH2:15]([Sn](CCCC)(CCCC)C=C)[CH2:16]CC.[Li+].[Cl-].CCOC(C)=O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:15]([C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH2:13][OH:14])=[CH2:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 66644089HCID 66644089, compound

Product 1

HCID 66646404HCID 66646404, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5-bromo-4-(2-hydroxyethyl)-2-benzofuran-1(3H)-one (0.460 g, 1.78 mmol), tributyl(vinyl)tin (0.676 g, 2.13 mmol), LiCl (0.224 g, 5.33 mmol) and Pd (PPh3)4 (0.10 g, 0.087 mmol) in toluene (50 mL) was heated at 100-110° C. under N2 overnight after which TLC indicated that the reaction had gone to completion. Next, EtOAc (100 mL) was poured into the solution and it was washed with brine, then water, then dried over Na2SO4, filtered and concentrated to dryness. The residue was then absorbed onto silica gel and separated over silica column to give the title compound.

Workup

  1. washwas washed with brine
  2. dry with materialwater, then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was then absorbed onto silica gel
  6. customseparated over silica column

Sources & evidence

ORD record
ord-882e2850586041afb5b2a6bda0d29365
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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