Chlorotrimethylsilane → HCID 86609491, compound

HRID 729231Notes

Reaction equation

HRID 729231 reaction equation
[CH:1]([NH:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)=[O:2].C(NC(C)C)(C)C.[Li].[CH3:17][Si:18](Cl)([CH3:20])[CH3:19]>C1COCC1>[CH3:17][Si:18]([CH3:20])([CH3:19])[C:5]1[S:6][CH:7]=[CH:8][C:4]=1[NH:3][CH:1]=[O:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 12571917HCID 12571917, compoundHCID 45051747Lithium diisopropylamine

Product 1

HCID 86609491HCID 86609491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

3- Formylaminothiophene (Bull. Soc. Chim. Fr. 1976,151) (2 g), dissolved in dry THF (20 ml), was dropped into a freshly prepared solution of lithium diisopropylamine (0.035 mol) in THF (35 ml) at −70° C. The solution was warmed to −20° C. and stirred for 30 minutes, then cooled again to −70° C., whereupon trimethylsilylchloride (5 ml) was added. After stirring for an additional hour at this temperature the mixture was slowly warmed to room temperature and stirred for 4 hours. Quenching with a saturated solution of ammonium chloride, extracting with ethyl acetate, drying over sodium sulfate, removing the solvent and applying chromatography on silica gel (hexane:ethyl acetate 2:1) yielded 2-trimethylsilyl-3-formylaminothiophene (1.2 g) (m.p. 74-76° C.).

Workup

  1. additionwas added
  2. stirringAfter stirring for an additional hour at this temperature the mixture
  3. temperaturewas slowly warmed to room temperature
  4. stirringstirred for 4 hours
  5. customQuenching with a saturated solution of ammonium chloride
  6. extractionextracting with ethyl acetate
  7. dry with materialdrying over sodium sulfate
  8. customremoving the solvent

Sources & evidence

ORD record
ord-c4590565dae74802aa63227ba0338a45
Source dataset
uspto-grants-2009_09
Patent number
US07582589B2

Reaction notes

Loading…