Dichloromethane → HCID 13349252、化合物

HRID 364334ノート

反応式

HRID 364334 の反応式
[Cl-].C([Al+][CH2:5][CH3:6])C.[CH2:7](Cl)Cl.CS(O[C@H]([C:17]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C)([OH:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])C)(=O)=O>P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:7][C@@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:5][CH3:6])[C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 13349246HCID 13349246、化合物HCID 16686102Diethyl aluminum chloride

生成物 1

HCID 13349252HCID 13349252、化合物収率 90%

試薬・触媒・溶媒 2

HCID 1004Phosphoric Acid触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

After 0.63 ml (0.63 mmol) of diethylaluminum chloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 89.7 mg (0.24 mmol) of (S)-2-methanesulfonyloxy-3-octyl-3-undecanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-10-methyl-9-octadecanone as a colorless oily substance (60.5 mg, yield 90%).

後処理

  1. stirringstirred for two and a half hours at -78° C.
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was separated

出典と根拠

ORDレコード
ord-524551429d3e4fc2bae4047df7efb279
出典データセット
uspto-grants-1986_08
特許番号
US04604486

反応ノート

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