Iodoethane → HCID 86705340, compound

HRID 587986Notes

Reaction equation

HRID 587986 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CC[CH2:39][CH2:38]1.C(I)C>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][C:14]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])([CH2:38][CH3:39])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 23714775LiHMDS tetrahydrofuranHCID 86705338HCID 86705338, compound

Product 1

HCID 86705340HCID 86705340, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Benzyloxycarbonylbutyl)thiophene-2-carboxylic acid tert-butyl ester (29.5 g, 78.8 mmol) was dissolved in tetrahydrofuran (200 mL), 1.09 M lithium bis(trimethylsilyl)azanide/tetrahydrofuran solution (94 mL, 102 mmol) was added dropwise at −78° C., and the mixture was stirred for 2 hours. To the reaction mixture was added ethyl iodide (12.3 g, 156 mmol) at −78° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was added to ethyl acetate and 0.5 N-hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with sodium thiosulfate solution and brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (24.9 g, 61.9 mmol, 78%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was added to ethyl acetate and 0.5 N-hydrochloric acid solution
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted two times with ethyl acetate
  6. washwashed with sodium thiosulfate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6970b3d29de43cdbd3d28e18fc79b9c
Source dataset
uspto-grants-2016_01
Patent number
US09227949B2

Reaction notes

Loading…