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

HRID 1840509노트

반응식

HRID 1840509 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0122586262d4a25adf0a64f4a296565
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680338B2

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