Sodium bis(trimethylsilyl)amide → 4-((3-(4-Chlorophenoxy)propylsulfanyl)methyl)-tetrahydropyran-4-carboxylic Acid

HRID 1840509Notes

Reaction equation

HRID 1840509 reaction equation
C([S:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[C:26]1(=[O:35])[C:29]2([CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH2:28][O:27]1>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][S:4][CH2:28][C:29]2([C:26]([OH:27])=[O:35])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 155411872,7-Dioxaspiro[3.5]nonan-1-oneHCID 234482731-Acetylsulfanyl-3-(4-chlorophenoxy)propane

Product 1

HCID 98845604-((3-(4-Chlorophenoxy)propylsulfanyl)methyl)-tetrahydropyran-4-carboxylic AcidYield 10.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of Intermediate 3 (0.80 g) in methanol was treated with a solution of sodium hexamethyldisilazide (1 M in THF, 3.3 ml) at 0° C. and the resulting mixture was stirred for 2 h, then a solution of Intermediate 1 (460 mg) in methanol was added. The mixture was stirred for 18 h, then evaporated and the residue dissolved in water and washed with diethyl ether. The aqueous phase was acidified with citric acid and extracted with dichloromethane; the organic layer was then washed with brine, dried over MgSO4 and evaporated to give the title compound (0.12 g) as a colourless oil.

Workup

  1. stirringThe mixture was stirred for 18 h
  2. customevaporated
  3. dissolutionthe residue dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with dichloromethane
  6. washthe organic layer was then washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-a0122586262d4a25adf0a64f4a296565
Source dataset
uspto-grants-2004_01
Patent number
US06680338B2

Reaction notes

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