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

HRID 21427

Reaction equation

HRID 21427 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 22850730(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoateYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-85bfe5171bf14946843aa1a406d7b425
Source dataset
uspto-grants-1995_06
Patent number
US05424005

Linked notes

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