Pyridine → HCID 54110445, compound

HRID 1940211Notes

Reaction equation

HRID 1940211 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][C:8]1[C:9]([CH3:22])=[C:10]([CH3:21])[C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:19]=1[CH3:20].N1C=CC=CC=1>ClCCl>[CH3:1][CH:2]([CH3:6])[C:3]([O:7][C:8]1[C:9]([CH3:22])=[C:10]([CH3:21])[C:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13](=[O:18])[C:12]=2[C:19]=1[CH3:20])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 10220089HCID 10220089, compound

Product 1

HCID 54110445HCID 54110445, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methylpropionylchloride (isobutyryl-chloride, 8.05 g, 75.55 mmol) in dichloromethane (10 mL) is added dropwise at 0° C. and under nitrogen to a solution of 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one (12.8 g, 58.11 mmol) and pyridine (5.97 g, 61 mmol) in dichloromethane (58 mL). The ice bath is removed and the mixture is stirred for 2 hrs at room temperature. Water (10 mL) is added and the organic phase is washed with 2N hydrochloric acid (100 mL), water (100 mL), 10% sodium bicarbonate (100 mL) and brine. The solution is dried (magnesium sulfate) and evaporated to dryness to give 17 g (100%) of 5-(2-methylpropionoxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one as an oil which is used without purification for the next step. Rf=0.5 (heptane/ethyl acetate 90:10)

Workup

  1. customThe ice bath is removed
  2. additionWater (10 mL) is added
  3. washthe organic phase is washed with 2N hydrochloric acid (100 mL), water (100 mL), 10% sodium bicarbonate (100 mL) and brine
  4. dry with materialThe solution is dried (magnesium sulfate)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7cd42df48a374fa6a916f5f25c038cff
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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