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

HRID 654553

反応式

HRID 654553 の反応式
[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

参加物

10

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-efae501d2a4f4bacb39b4fd990cc6ca9
出典データセット
uspto-grants-1992_07
特許番号
US05132328

関連ノート

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