Triethylamine → Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester

HRID 21423

Reaktionsgleichung

Reaktionsgleichung von HRID 21423
[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][CH: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 14549213Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl esterAusbeute 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 drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), 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, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g).

Aufarbeitung

  1. waitThe mixture was left
  2. customThe methylene chloride layer separated
  3. washwas washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled
  6. customto obtain a crude objective compound
  7. customThe compound was purified by toluene/silica gel chromatography and recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b0bbf4059f3f4f6985f90088f6ed8e04
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424005

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