Triphenylphosphine → tert-butyl (2R)-(+)-2-[4'-(2",4"-dichlorophenoxy)phenoxy]propionate

HRID 1381752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381752
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[Cl:11][C:12]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:11][C:12]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:3][C@H:2]([CH3:4])[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 945094-(2,4-Dichlorophenoxy)phenolHCID 5462977Diethyl azodicarboxylateHCID 129438461,1-Dimethylethyl (2S)-2-hydroxypropanoate

Produkt 1

HCID 54334601tert-butyl (2R)-(+)-2-[4'-(2",4"-dichlorophenoxy)phenoxy]propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of known tert-butyl L-(+)-lactate (0.88 g), 4-(2',4'-dichlorophenoxy)phenol (1.54 g) and triphenylphosphine (1.58 g) in dry tetrahydrofuran (58 ml) on an ice bath, diethylazodicarboxylate (0.95 ml) was added dropwise. After the addition, the ice bath was removed and the mixture was further stirred at room temperature for 25 hours. The reaction mixture was evaporated with a rotary evaporator. The residue thus obtained was purified by silica gel chromatography [silica gel 399 g, eluant:ethyl acetate-hexane (1:30)] to give tert-butyl (2R)-(+)-2-[4'-(2",4"-dichlorophenoxy)phenoxy]propionate as a colorless oily substance (0.98 g). This was left to stand at room temperature under high vacuum (0.25 Torr) for 2 hours and under atmosphere for several days to crystallize. A crystalline substance thus formed was washed with a small amount of hexane and filtered to give colorless crystals.

Aufarbeitung

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction mixture was evaporated with a rotary evaporator
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography [silica gel 399 g, eluant:ethyl acetate-hexane (1:30)]

Quellen und Nachweise

ORD-Eintrag
ord-b42d6c631566498e8b6f92e7898087bb
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803301

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