1,2-Dibromoethane → (2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl ester

HRID 459300

반응식

HRID 459300 반응식
[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Mg+2].[CH2:29](Br)[CH2:30][Br:31]>CCO>[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:29][CH2:30][Br:31])=[CH:11][CH:12]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 78391,2-Dibromoethane2회HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11390460HCID 11390460, 화합물

생성물 1

HCID 58822865(2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture containing (2S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester obtained in Step 1 (0.223 mol, 50 mg), potassium carbonate (0.446 mol, 50 mg), magnesium sulfate (powdered, 50 mg, 1 g/g), ethylene dibromide (3.35 mol. 628 mg) and EtOH (25 mL) was heated at reflux (78–76° C.) for 24 hours and cool to room temperature. The mixture was heated again to reflux (76.5–77° C.) and 2 mL of ethylene dibromide was added. The mixture was heated for another 12 hours at 79.5–80.1° C. and then cooled to room temperature and vacuum filtered. The filtrate was concentrated under vacuum, and the residue was purified by column chromatography (silica gel, hexanes/ethyl acetate 6:1, Rf 027) to produce a colorless oil. MS (ES) for C14H19BrO4 [M+Na]+: 353.0.

후처리

  1. temperaturewas heated
  2. temperatureat reflux (78–76° C.) for 24 hours
  3. temperatureThe mixture was heated again
  4. additionwas added
  5. temperatureThe mixture was heated for another 12 hours at 79.5–80.1° C.
  6. temperaturecooled to room temperature
  7. filtrationvacuum filtered
  8. concentrationThe filtrate was concentrated under vacuum
  9. customthe residue was purified by column chromatography (silica gel, hexanes/ethyl acetate 6:1, Rf 027)
  10. customto produce a colorless oil

출처 및 근거

ORD 기록
ord-9bdce17b3f9745cbabd0c9c4b53ffb28
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192982B2

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