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Hydrochloric Acid → (R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetate

HRID 633475
ノート
印刷プレビュー

反応式

HRID 633475 の反応式
[OH:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22].Cl>CN(C)C1C=CN=CC=1.ClCCl>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([O:1][C@H:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:3]([O:5][CH3:6])=[O:4])(=[O:32])=[O:31])=[CH:28][CH:29]=1)([O-:23])=[O:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

生成物 1

HCID 45114280(R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetate収率 98%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

0.72 g (6 mmoles; 0.1 equivalent) of 4-dimethylaminopyridine, 12.0 g (60 mmoles; 1 equivalent) of methyl(R)-2-hydroxy-2(2-chlorophenyl)acetate and 7.8 g (78 mmoles; 1.3 equivalent) of triethylamine and 20 ml of dichloromethane were added to a dry reaction flask. The colorless solution obtained was cooled to 0° C. and then, operating at this temperature, 13.14 g (60 mmoles; 1 equivalent) of 4-nitrobenzenesulfonyl chloride as a solution in 30 ml of dichloromethane was added. The reaction mixture was stirred for 3 hours at 0° C. and 240 ml of 1N hydrochloric acid and 240 ml of dichloromethane was added drop wise, while stirring this mixture. After decanting, the dichloromethane phase is washed with dilute hydrochloric acid and then with water, before being concentrated under reduced pressure. An analytically pure sample is obtained after purifying on a silica column. In this manner, methyl(R)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate is obtained: Yield: 98%. Optical purity: 99%.

後処理

  1. customThe colorless solution obtained
  2. additionwas added
  3. stirringwhile stirring this mixture
  4. customAfter decanting
  5. washthe dichloromethane phase is washed with dilute hydrochloric acid
  6. concentrationwith water, before being concentrated under reduced pressure
  7. customAn analytically pure sample is obtained
  8. customafter purifying on a silica column

出典と根拠

ORDレコード
ord-7fff9e5a18f744c89870a6e81b8041c9
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321785B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート