Sodium Acetate → methyl (S)-4-bromo-3-hydroxybutyrate

HRID 1657056ノート

反応式

HRID 1657056 の反応式
Br[CH:2]([CH:7]([OH:10])[CH2:8][Br:9])[C:3]([O:5][CH3:6])=[O:4].C([O-])(=O)C.[Na+]>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[Br:9][CH2:8][C@@H:7]([OH:10])[CH2:2][C:3]([O:5][CH3:6])=[O:4]

参加物

6

反応物 2

HCID 517045Sodium AcetateHCID 14168306Methyl 2,4-dibromo-3-hydroxy-butanoate

生成物 1

HCID 11960268methyl (S)-4-bromo-3-hydroxybutyrate

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

An argon purged solution of the dibromide obtained in step (b) above (20.8 g, 75.4 mM) and anhydrous sodium acetate (NaOAc) (21.0 g) in ethyl acetate (370 ml) and glacial acetic acid (37 ml) was treated with 5% Pd/C (1.30 g) and the black suspension stirred under one atmosphere of H2 while monitoring uptake (22.4 l/mole). After 2.0 hours H2 uptake was complete, the mixture was filtered through Celite, the filtrate washed with saturated NaHCO3 and brine and then dried over anhydrous MgSO4 and evaporated to give the crude bromoester title product as a brown oil. The crude oil was combined with another batch (starting from 36.77 g of the dibromide) and vacuum distilled to give 25.771 g (61.3%) of the pure bromoester title product as a clear oil with b.p.=79°-80° C. (1.0 mm Hg) and with consistent C13NMR spectral data. TLC (1:1) ethyl acetatehexane, Rf=0.44, PMA.

後処理

  1. filtrationthe mixture was filtered through Celite
  2. washthe filtrate washed with saturated NaHCO3 and brine
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated

出典と根拠

ORDレコード
ord-c1c07e0e76264453a0d5b0005fa4f701
出典データセット
uspto-grants-1993_10
特許番号
US05256692

反応ノート

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