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

HRID 1840509ノート

反応式

HRID 1840509 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a0122586262d4a25adf0a64f4a296565
出典データセット
uspto-grants-2004_01
特許番号
US06680338B2

反応ノート

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