Hydrochloric Acid → HCID 178501146、化合物

HRID 528698ノート

反応式

HRID 528698 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)=[O:14].C(N(CC)CC)C.Cl>ClCCl>[CH3:11][O:12][C:13]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[CH2:17][CH2:16]1)=[O:14]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178501147HCID 178501147、化合物

生成物 1

HCID 178501146HCID 178501146、化合物収率 107.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-50 °C

実験手順

To a solution of dimethylsulfoxide (9.53 g, 122 mmol) in dry dichloromethane (400 ml) was slowly added oxalyl chloride (7.74 g, 61.0 mmol) at −78° C. The cooling bath was removed and the reaction mixture was stirred at −50° C. for 5 min. A solution of trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (8.75 g, 50.8 mmol) in dichloromethane (108 ml) was added at −65° C. Stirring for 30 minutes was followed by addition of triethylamine (25.7 g, 254 mmol). The cooling bath was removed 15 minutes after completed addition. The reaction mixture was quenched with 1 M aqueous hydrochloric acid solution (152 ml, 152 mmol) at −10° C. The layers were separated. The organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as yellow oil (9.3 g, quantitative), which was used in the next step without further purification. MS m/e: 170 (M+)

後処理

  1. customat −78° C
  2. customThe cooling bath was removed
  3. stirringStirring for 30 minutes
  4. customThe cooling bath was removed 15 minutes
  5. additionaddition
  6. customThe layers were separated
  7. washThe organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-79435c97d24749389e274427184c3df1
出典データセット
uspto-grants-2016_05
特許番号
US09346824B2

反応ノート

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