Toluene → (3S)-oxolan-3-yl carbonochloridate

HRID 2062177

Reaktionsgleichung

Reaktionsgleichung von HRID 2062177
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[C:7](Cl)([Cl:9])=[O:8].C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:9][C:7]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 6371PhosgeneHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Produkt 1

HCID 22876378(3S)-oxolan-3-yl carbonochloridateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of (S)-tetrahydrofuran-3-ol (7.9 g, 90 mmol) in anhydrous CH2Cl2 (50 mL) under an N2 atmosphere was cooled in an ice bath, and a 20% solution of phosgene in toluene (134 mL, 270 mmol) was slowly added. The reaction was allowed to warm to room temperature overnight, and the solvent was removed under vacuum to afford (S)-tetrahydrofuran-3-yl chloroformate (12.1 g, 85%) as a clear liquid. 1H NMR (400 MHz, CDCl3) δ 5.42-5.39 (m, 1H), 4.01-3.84 (m, 4H), 2.31-2.13 (m, 2H).

Aufarbeitung

  1. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-faaae9397228433ba372fb9d7750843f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283354B2

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