Potassium bis(trimethylsilyl)amide → HCID 69038734, compound

HRID 1820793Notes

Reaction equation

HRID 1820793 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])(=[O:7])=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[CH:4]1([S:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=2)[C:13]([OH:15])=[O:14])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69036283HCID 69036283, compound

Product 1

HCID 69038734HCID 69038734, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To 8.0 mmol 5-(3-chloro-propane-1-sulfonyl)-2-hydroxy-benzoic acid in 30 ml THF at −78° C. was added dropwise over 30 min 23.9 mmol of a 0.9 M solution of potassium bis(trimethylsilyl)amide in toluene. The reaction mixture was then allowed to warm to RT and stirring continued for a further 30 min at RT. The mixture was then diluted with THF/ethyl acetate (1:1) and washed sequentially with 1 M aq HCl and saturated aqueous NaCl solution, dried with Na2SO4, and concentrated in vacuo. The residue was triturated in ether/pentane to afford the title compound. MS (m/e): 241.2 ([M−H]−, 100%)

Workup

  1. washwashed sequentially with 1 M aq HCl and saturated aqueous NaCl solution
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in ether/pentane

Sources & evidence

ORD record
ord-b4943ad06330473ba00d3b804ffd4239
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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