Triethylamine → (R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

HRID 21427

Reaktionsgleichung

Reaktionsgleichung von HRID 21427
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C@H:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:27][C@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:19]([F:18])([F:28])[F:29])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

Produkt 1

HCID 22850730(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoateAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g) ([α]D22.5 =+20.1, optical purity 96.3 % ee), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml) under ice-cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order before being dried over magnesium sulfate. After distillation was over purification by toluene/silica gel chromatography and recrystallization from ethanol gave the titled compound (3.8 g).

Aufarbeitung

  1. temperaturecooling
  2. waitThe mixture was left
  3. customThe methylene chloride layer separated
  4. washwas washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order
  5. dry with materialbefore being dried over magnesium sulfate
  6. distillationAfter distillation
  7. customwas over purification by toluene/silica gel chromatography and recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-85bfe5171bf14946843aa1a406d7b425
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424005

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