HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → (R)-(+)-4-octyloxyphenyl 4'-(1,1,1-trifluoro-2-octyloxycarbonyl)biphenyl-4-carboxylate

HRID 257404
Notes
Print preview

Reaction equation

HRID 257404 reaction equation
[F:1][C:2]([F:29])([F:28])[CH:3]([O:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25](Cl)=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:30]([O:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl.O>[F:1][C:2]([F:29])([F:28])[C@H:3]([O:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:45][C:42]3[CH:41]=[CH:40][C:39]([O:38][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:44][CH:43]=3)=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 77412Phenol, 4-(octyloxy)-HCID 541276134'-(1,1,1-Trifluoro-2-octyloxycarbonyl)biphenyl-4-carbonylchloride

Product 1

HCID 22848632(R)-(+)-4-octyloxyphenyl 4'-(1,1,1-trifluoro-2-octyloxycarbonyl)biphenyl-4-carboxylateYield 42.9%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4'-(1,1,1-trifluoro-2-octyloxycarbonyl)biphenyl-4-carbonylchloride (1.3 g) and 4-n-octyloxyphenol (1.0 g) in methylene chloride (40 ml) were added triethylamine (0.5 g) and dimethylaminopyridine (0.032 g). The mixture was stirred for 24 hours at room temperature before it was poured in water. Extraction was made with methylene chloride and the extract was washed with dilute aqueous sodium carbonate solution and water, in this order and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (developer hexane ethyl acetate 10 0.5) and recrystallized from ethanol to obtain the titled compound (0.8 g).

Workup

  1. extractionExtraction
  2. washthe extract was washed with dilute aqueous sodium carbonate solution and water, in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (developer hexane ethyl acetate 10 0.5)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-216c0a7ea4f64eaaaae9abe9811df019
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05262086

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes