Diethyl Ether → HCID 18630385, compound

HRID 1458110Notes

Reaction equation

HRID 1458110 reaction equation
[Li+].CC([N-]C(C)C)C.CCOCC.[CH2:14]([NH:16][C:17](=[O:26])[C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[Cl:25])[CH3:15].[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>C1COCC1>[Cl:24][C:22]1[C:23]([Si:28]([CH3:30])([CH3:29])[CH3:27])=[C:18]([C:19]([Cl:25])=[CH:20][CH:21]=1)[C:17]([NH:16][CH2:14][CH3:15])=[O:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 690464HCID 690464, compoundHCID 2724682Lithium diisopropylamide

Product 1

HCID 18630385HCID 18630385, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-100 °C

Procedure

A solution of 1.5M LDA in THF (13 mL, 19.5 mmol) was added dropwise to an ether/liquid N2 cooled solution of N-ethyl 2,5-dichlorobenzamide (2.0 g, 9.2 mmol) and TMSCl (1.5 mL, 11.5 mmol) in THF (50 mL), maintaining the internal reaction temperature ≤-80° C. The resulting reaction mixture was stirred at -100° C. for 30 min, then was partitioned between ether and sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and crystallized from EtOAc/hexanes to afford 1.15 g of the title compound as a white solid. m.p. 150°-153° C.

Workup

  1. temperaturemaintaining the internal reaction temperature ≤-80° C
  2. customThe resulting reaction mixture
  3. customwas partitioned between ether
  4. dry with materialThe ether solution was dried (MgSO4)
  5. concentrationconcentrated
  6. customcrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-448e5b77cb3d4040bd355f6ecc678bce
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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