Dichloromethane → Methyl 2-methanesulfonyloxy-3-phenyl-propionate

HRID 1613899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613899
ClCCl.[OH:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.CCOCC>[CH3:24][S:25]([O:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:27])=[O:26]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 518800Methyl 2-hydroxy-3-phenylpropanoate

Produkt 1

HCID 13662406Methyl 2-methanesulfonyloxy-3-phenyl-propionateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881112Ethyl ether methylene chlorideLösungsmittel

Versuchsvorschrift

A dichloromethane solution of methyl 2-hydroxy-3-phenylpropionate (33) is treated with triethylamine (1.1 equiv) and methanesulfonyl chloride (1.1 equiv) at 0° C. Upon completion of reaction, the mixture is dissolved in dichloromethane/ether and washed with saturated aqueous solution of sodium chloride, dried and concentrated. Purification of crude material by flash column chromatography (40% ethyl acetate in hexane) gives methyl 2-methanesulfonyloxy-3-phenylpropionate (1.6 g, 93%). 1H NMR (300 MHz CDCl3): δ 7.358-7.233 (m, 5H), 5.173 (dd, 4.26 Hz, 8.8 Hz, 1H), 3.793 (s, 3H), 3.301 (dd, 4.23 Hz, 14.38 Hz, 1H), 3.1295 (dd, 8.8 Hz, 14.3 Hz, 1H), 2.766 (s, 3H).

Aufarbeitung

  1. customUpon completion of reaction
  2. washwashed with saturated aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customPurification of crude material by flash column chromatography (40% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-19bd6031de0f4784b9594288ab4a0b5a
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194605

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