Ethyl bromoacetate → Acetic acid, (p-tolylsulfonyl)-, ethyl ester

HRID 481097

反応式

HRID 481097 の反応式
COC1N=C(C[S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])C([N+]([O-])=O)=CC=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH3:29]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 136265146-Methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine

生成物 1

HCID 76102Acetic acid, (p-tolylsulfonyl)-, ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5.0 g (15.5 mmol) of 6-methoxy-3-nitro-2-(toluene-4-sulfonyl methyl)-pyridine and 1.8 mL (16 mmol) of ethyl bromoacetate is dissolved in 20 mL of DMF. To this solution is added 4.4 g (32 mmol) of K2CO3 and the reaction mixture is heated to 50° C. for 18 hours. The reaction mixture is cooled to room temperature and diluted with 300 mL of water. The mixture is extracted with ethyl acetate. The ethyl acetate extracts are dried (Na2SO4) and evaporated to yield 7.2 grams of 6-methoxy-3-nitro-pyridin-2-yl]-[toluene-4-sulfonyl]-acetic acid ethyl ester. 1H NMR (CDCl3) δ8.30 (d, 1H), 7.60 (d, 2H), 7.30 (d, 2H), 6.80 (d, 1H), 6.30 (m, 1H), 4.0 (q, 2H), 3.80 (s, 3H), 3.60 (m, 1H), 3.10 (m, 1H), 2.40 (s, 3H), 1.10 (t, 3H). Mass spectrum: m/e=409.0 (p+1). TLC (7/3: hexanes/ethyl acetate) Rf=0.5.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialThe ethyl acetate extracts are dried (Na2SO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-97ab4a5da0c1460097e7333967f6bea6
出典データセット
uspto-grants-2003_11
特許番号
US06653471B2

関連ノート

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