4-Methoxymethyl-2-phenyl-thiazole-5-carboxylic Acid Methoxy-methyl Amide → 1-(4-Methoxymethyl-2-phenyl-thiazol-5-yl)-ethanone

HRID 396388노트

반응식

HRID 396388 반응식
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][CH3:19])=[O:5].[CH3:21][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[CH3:19][O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:10][C:6]=1[C:4](=[O:5])[CH3:21]

참가 물질

5

반응물 3

HCID 213547804-Methoxymethyl-2-phenyl-thiazole-5-carboxylic Acid Methoxy-methyl AmideHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 98781591-(4-Methoxymethyl-2-phenyl-thiazol-5-yl)-ethanone수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the above-prepared 4-methoxymethyl-2-phenyl-thiazole-5-carboxylic acid methoxy-methyl amide (6.706 g, 22.9 mmole, 1.0 eq) in dry THF (25 ml) at 0° C. was added dropwise a solution of 1.4M methylmagnesium bromide in (3:1)toluene-THF (32.7 ml, 45.8 mmole, 2.0 eq). The resulting tan suspension was stirred under nitrogen at room temperature for 30 minutes, then quenched by the addition of saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a brown oil. Silica gel chromatography using a gradient elution of (9:1) to (4:1) hexanes-ethyl acetate provided the title compound (6.033 g, 81%) as a yellow crystalline solid. 1H NMR (CDCl3): δ 2.7 (s, 3H), 3.5 (s, 3H), 4.9 (s, 2H) 7.4-7.5 (m, 3H), 8.0 (m, 2H).

후처리

  1. customquenched by the addition of saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. washa gradient elution of (9:1) to (4:1) hexanes-ethyl acetate

출처 및 근거

ORD 기록
ord-8de9488206cc44e58d5fa5c2a2061221
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608087B1

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