Water → 3-[2-(Methoxyethoxymethoxy)ethyl]-2-methylthiothiophene

HRID 1651645노트

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HRID 1651645 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15].C([Li])CCC.[CH3:21][S:22]SC.O>CCOCC.CCCCCC.C1COCC1>[CH3:15][O:14][CH2:13][CH2:12][O:11][CH2:10][O:9][CH2:8][CH2:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[S:22][CH3:21]

참가 물질

8

반응물 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 540438672-Bromo-3-[2-(methoxyethoxymethoxy)ethyl]thiopheneHCID 178418339Butyllithium

생성물 1

HCID 147004063-[2-(Methoxyethoxymethoxy)ethyl]-2-methylthiothiophene수율 75.4%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a stirred solution of 2-bromo-3-[2(methoxyethoxymethoxy)ethyl]thiophene (51.8 g, 0.175 mol) in anhydrous ether (125 ml) cooled to -70° C. was added n-butyl lithium (109.4 ml of a 1.6M solution in hexane, 0.175 mol) under a nitrogen atmosphere over a 11/2 hour period. A tan suspension resulted which was stirred for an additional 1 hour and then was diluted with dry THF (100 ml) and was passed under nitrogen into a stirred solution of dimethyldisulfide (18.8 g, 0.20 mol) in anhydrous ether (50 ml) at -15° C. The resulting mixture was stirred at -15° C. for 1/2 hour and at reflux for 2 hours. The dark mixture was cooled to 0° C. and water (100 ml) was added carefully. The organic layer was separated and washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature. The crude liquid (44.6 g) was distilled, the product being collected at 110-140° C. at 0.7 mm to give 34.6 g of pure product. Yield 75%. NMR supported the structure.

후처리

  1. customA tan suspension resulted which
  2. stirringThe resulting mixture was stirred at -15° C. for 1/2 hour
  3. temperatureat reflux for 2 hours
  4. customThe organic layer was separated
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo at room temperature
  9. distillationThe crude liquid (44.6 g) was distilled
  10. customthe product being collected at 110-140° C. at 0.7 mm

출처 및 근거

ORD 기록
ord-9138027154944896833ad8eba050cb25
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04929637

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