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

HRID 529998노트

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HRID 529998 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
5 °C

실험 절차

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=42 Hz, 1H), 2.52-2.68 (m, 2H).

후처리

  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)

출처 및 근거

ORD 기록
ord-e6ab91237c684a90b70759f606c89db9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351962B2

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