Chlorotrimethylsilane → HCID 18433505, compound

HRID 2306270Notes

Reaction equation

HRID 2306270 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.C([Li])(CC)C.[CH3:43][Si:44](Cl)([CH3:46])[CH3:45]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][Si:20]([CH:21]([CH3:22])[CH3:23])([CH:24]([CH3:26])[CH3:25])[CH:27]([CH3:29])[CH3:28])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[Si:44]([CH3:46])([CH3:45])[CH3:43])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 18433611HCID 18433611, compoundHCID 178418400CID 536281002×

Product 1

HCID 18433505HCID 18433505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(tert-butoxycarbonylamino)-7-(triisopropylsilyloxy) naphthalene, as described above in Step A, (12.47 g, 30.0 mmol) and N,N,N′,N′-tetramethylethylenediamine (10.0 mL, 66.0 mmol) in THF (300 mL) at −78° C. was added sec-butyllithium (1.3 M in cyclohexane, 24.2 mL, 31.5 mmol) dropwise. The reaction mixture was stirred at −78° C. for 5 min, then trimethylsilyl chloride (4.2 mL, 33.0 mmol) was added dropwise and stirring was continued for 30 min. sec-Butyllithium (1.3 M in cyclohexane, 24.2 mL, 31.5 mmol) was added and the mixture was stirred dropwise was stirred at −78° C. for 5 hours, then quenched with saturated aqueous NH4Cl (400 mL) and extracted with CH2Cl2 (2×500 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—30% to 50% CH2Cl2 to yield the above-titled product.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min.
  3. stirringthe mixture was stirred dropwise
  4. stirringwas stirred at −78° C. for 5 hours
  5. customquenched with saturated aqueous NH4Cl (400 mL)
  6. extractionextracted with CH2Cl2 (2×500 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash column chromatography on silica
  11. washeluting with a gradient of hexane—30% to 50% CH2Cl2

Sources & evidence

ORD record
ord-566756641f42477cb9d6083402122e38
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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