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

HRID 497415

반응식

HRID 497415 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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) δ 8.30 (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. Step 3:

후처리

  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

출처 및 근거

ORD 기록
ord-cb271b46556548aebf195e13a84d822a
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949562B2

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