Water → HCID 15452329, compound

HRID 378082Notes

Reaction equation

HRID 378082 reaction equation
[Li]CCCC.[CH2:6]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[O:10])[CH3:7].[CH3:16][Si:17](Cl)([CH3:19])[CH3:18].O>CCCCCC.C1COCC1>[CH2:6]([NH:8][C:9]([C:11]1[S:12][C:13]([Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:14][C:15]=1[Si:17]([CH3:19])([CH3:18])[CH3:16])=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 5151566Thiophenecarboxamide,N-ethyl-HCID 178418339Butyllithium

Product 1

HCID 15452329HCID 15452329, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 2.5M n-BuLi in hexane (18 mL) was added dropwise to a solution of N-ethyl-2-thiophenecarboxamide (3.1 g, 20 mmol) in 50 mL THF at below -65° C. under a positive nitrogen atmosphere and the resulting solution was stirred at -70° C. for 45 min. After that, TMSCl (9 mL) was added slowly at below -60° C. and stirring was continued at below -60° C. for 15 min. The solution was allowed to warm to 0° C., then poured into water and extracted with CH2Cl2. The organic layer was separated, washed with brine, dried and concentrated. Flash chromatography of the residue with 5% ethyl acetate-hexane yielded 3.1 g of Example 248 as a white solid, m.p. 81-84° C., and 1.1 g of Example 249 as a colorless oil. nD24 1.5228.

Workup

  1. stirringstirring
  2. waitwas continued at below -60° C. for 15 min
  3. temperatureto warm to 0° C.
  4. extractionextracted with CH2Cl2
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-30dd0f643cc94c64a76c6bedcbc6b2c9
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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