Chlorotrimethylsilane → HCID 10713229, compound

HRID 356393Notes

Reaction equation

HRID 356393 reaction equation
[Li]C(CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.CN(CCN(C)C)C.[CH2:27]([N:29]([CH:39]([O:44][CH3:45])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:30](=[O:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:37])[CH3:28].[CH3:46][Si:47](Cl)([CH3:49])[CH3:48]>C1COCC1>[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([Si:47]([CH3:49])([CH3:48])[CH3:46])[C:31]=1[C:30]([N:29]([CH2:27][CH3:28])[CH:39]([O:44][CH3:45])[C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38]

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 10564951HCID 10564951, compoundHCID 18522661Acetone cardiceHCID 178418400CID 53628100

Product 1

HCID 10713229HCID 10713229, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (3.53 mL, 4.59 mmol) was added to a dry ice/acetone cooled solution of TMEDA (639 mL, 4.23 mmol) and N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)-2-chlorobenzamide (1.0 g, 3.53 mmol) in THF (7 mL). The resulting mixture was stirred at -78° C. for 45 min, then TMSCl (671 mL, 5.29 mmol) was added in a single portion. The reaction was allowed to warm to 0° C., and partitioned between ether and 10% HCl. The ether solution was then extracted with sat aq NaHCO3, dried (MgSO4), and purified by RC with 1:49 EtOAc/hexanes to afford 750 mg of the title compound as a white solid, a 60% yield. m.p. 82°-83° C.

Workup

  1. temperatureto warm to 0° C.
  2. custompartitioned between ether and 10% HCl
  3. extractionThe ether solution was then extracted with sat aq NaHCO3
  4. dry with materialdried (MgSO4)
  5. custompurified by RC with 1:49 EtOAc/hexanes

Sources & evidence

ORD record
ord-58912df7421742d48d35b2d504e930b5
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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