Sodium Hydroxide → HCID 58566790, compound

HRID 2069687Notes

Reaction equation

HRID 2069687 reaction equation
[OH-].[Na+].N1CCC[C@H]1C(O)=O.I[C:12]1[CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]2[O:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]=2[CH:22]=1.[CH3:28][S:29]([O-:31])=[O:30]>CS(C)=O.[Cu]I.O>[CH3:20][C:18]1([CH3:21])[CH2:17][C:16]2[CH:22]=[C:12]([S:29]([CH3:28])(=[O:31])=[O:30])[CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]=2[O:19]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 3870744MethanesulfinateHCID 58566704HCID 58566704, compound

Product 1

HCID 58566790HCID 58566790, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (11.5 mg, 0.288 mmol) was added to a solution of L-proline (33.1 mg, 0.288 mmol) in DMSO (3 mL) and stirred for 30 minutes. To this solution was added ethyl 5-iodo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (829) (500 mg, 1.44 mmol), methane sulfinate (176.6 mg, 1.73 mmol), and copper (I) iodide (27.4 mg, 0.144 mmol) and the reaction was stirred for 18 hours at 80° C. Water (20 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel chromatography (eluting with 0-60% ethyl acetate in hexane) to provide ethyl 2,2-dimethyl-5-(methylsulfonyl)-2,3-dihydrobenzofuran-7-carboxylate (830) (186.9 mg, 44%).

Workup

  1. stirringthe reaction was stirred for 18 hours at 80° C
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (eluting with 0-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1c4822ef57944ce4af6f8d34066d3527
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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