Acetoin → (2RS,3SR)-2-(3-benzyloxy-5-fluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol

HRID 654553

반응식

HRID 654553 반응식
[Si:1]([O:8][CH:9]([CH3:13])[C:10](=[O:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].OC(C)C(=O)C.[Si](Cl)(C(C)(C)C)(C)C.N1C=CN=C1.[CH2:33]([O:40][C:41]1[CH:42]=[C:43]([Mg]Br)[CH:44]=[C:45]([F:47])[CH:46]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.BrC1C=C(OCC2C=CC=CC=2)C=C(F)C=1.[Mg]>C(OCC)C.O1CCCC1>[CH2:33]([O:40][C:41]1[CH:42]=[C:43]([C:10]([OH:12])([CH:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH3:13])[CH3:11])[CH:44]=[C:45]([F:47])[CH:46]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

10

반응물 7

HCID 179AcetoinHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5462224MagnesiumHCID 110418312-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-HCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 178505958HCID 178505958, 화합물

생성물 1

HCID 19761503(2RS,3SR)-2-(3-benzyloxy-5-fluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol수율 41%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 3-tert-butyldimethylsilyloxybutan-2-one (5.56 g; prepared by reacting 3-hydroxybutan-2-one with tert-butyldimethylsilyl chloride in diethyl ether and using imidazole as a suitable base) in tetrahydrofuran (5 ml) was added to a solution of 3-benzyloxy-5-fluorophenylmagnesium bromide [prepared by heating a mixture of benzyl 3-bromo-5-fluorophenyl ether (6.7 g), magnesium powder (0.58 g) and tetrahydrofuran (50 ml) to 40° C. for 1 hour] in tetrahydrofuran (50 ml) and the mixture was stirred at ambient temperature for 2.5 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and water. The organic phase was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 3:2 v/v mixture of petroleum ether (b.p. 40°-60° C.) and methylene chloride as eluent. There was thus obtained an erythro isomer, (2RS,3SR)-2-(3-benzyloxy-5-fluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol (3.8 g, 41%), as an oil; and a threo isomer, the corresponding (2RS,3RS)-isomer (1.73 g, 18%), as an oil.

후처리

  1. customprepared
  2. customprepared
  3. temperatureby heating
  4. customThe mixture was evaporated
  5. customthe residue was partitioned between diethyl ether and water
  6. washThe organic phase was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. additiona 3:2 v/v mixture of petroleum ether (b.p. 40°-60° C.) and methylene chloride as eluent

출처 및 근거

ORD 기록
ord-efae501d2a4f4bacb39b4fd990cc6ca9
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05132328

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