Triphenylphosphine → Methyl (R)-4-Chloro-3-hydroxybutyrate

HRID 1855231ノート

反応式

HRID 1855231 の反応式
[OH:1][C@@H:2]([CH2:8]O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Cl:36])C(=O)C1>C(Cl)Cl>[Cl:36][CH2:8][C@H:2]([OH:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 9877378methyl (3R)-3,4-dihydroxybutanoate

生成物 1

HCID 10920707Methyl (R)-4-Chloro-3-hydroxybutyrate収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

To a solution of (R)-methyl 3,4-dihydroxybutanoate (125.1 g, 0.93 mol) in CH2Cl2 (1.8 L) was added PPh3 (244.5 g, 0.93 mol) and slowly added NCS (124.2 g, 0.93 mol) under ice water cooling. The mixture was stirred at 5° C. for 20 min and then stirred for 18 h at room temperature. After evaporating the solvent, the residue was purified by column chromatography (P.E\E.A 20:1-5:1, gradient) to give (R)-methyl 4-chloro-3-hydroxybutanoate (33 g, 26% over 3 steps). 1H NMR (300 MHz, CDCl3) δ 4.18-4.25 (m, 1H), 3.68 (s, 3H), 3.55-3.60 (m, 2H), 3.32-3.33 (d, J=4.2 Hz, 1H), 2.52-2.68 (m, 2H).

後処理

  1. stirringstirred for 18 h at room temperature
  2. customAfter evaporating the solvent
  3. customthe residue was purified by column chromatography (P.E\E.A 20:1-5:1, gradient)

出典と根拠

ORDレコード
ord-90a1c93a6b8e4932b8519de00d09528a
出典データセット
uspto-grants-2015_02
特許番号
US08962856B2

反応ノート

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