Chloroform → (-)-2-Phenoxypropyl tosylate

HRID 1112624

Reaktionsgleichung

Reaktionsgleichung von HRID 1112624
[O:1]([CH:8]([CH3:11])[CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>N1C=CC=CC=1>[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:10][CH2:9][CH:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:11])(=[O:18])=[O:17]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 201292-Phenoxy-1-propanol

Produkt 1

HCID 22762443(-)-2-Phenoxypropyl tosylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

(-)-2-Phenoxypropanol [α]D25 = -38.95° (c. 0.9, CHCl3) was treated with tosylchloride in pyridine to give the corresponding (-)-2-phenoxypropyl tosylate of which 1.10 g. was reacted with LiPPh2 following Example 28 to give 0.87 g. of (+)-2-phenoxypropyl diphenylphosphine having [α]D25 = +27.90° (c. 3.03, CHCl3).

Quellen und Nachweise

ORD-Eintrag
ord-b314cc77bdb546f283452703c473f565
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04123465

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