4-Fluorobenzoic Acid → HCID 178460891, compound

HRID 234557Notes

Reaction equation

HRID 234557 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.[CH3:26][Si:27]1([CH2:40][CH2:41][CH3:42])[CH2:32][CH2:31][CH:30]([C@H:33]2[CH2:38][CH2:37][C@H:36](O)[CH2:35][CH2:34]2)[CH2:29][CH2:28]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([O:23][C@H:36]2[CH2:35][CH2:34][C@H:33]([CH:30]3[CH2:29][CH2:28][Si:27]([CH3:26])([CH2:40][CH2:41][CH3:42])[CH2:32][CH2:31]3)[CH2:38][CH2:37]2)=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 178460890HCID 178460890, compound

Product 1

HCID 178460891HCID 178460891, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.50 g of N,N'-dicyclohexylcarbodiimide (DCC) was added to a mixture of 1.80 g of 4-fluorobenzoic acid, 2.54 g of trans-4-(4-methyl-4-n-propyl-4-silacyclohexyl)cyclohexanol, 1.50 g of 4-dimethylaminopyridine and 30 ml of methylene chloride at room temperature. The resultant reaction mixture was agitated for 8 hours at room temperature, after which the resultant N,N'-dicyclohexyl urea was removed by filtration. The filtrate was washed with brine, dried and concentrated to obtain a residue, followed by silica gel chromatography to obtain 2.12 g (yield: 56%) of the intended product.

Workup

  1. customThe resultant reaction mixture
  2. customafter which the resultant N,N'-dicyclohexyl urea was removed by filtration
  3. washThe filtrate was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a residue

Sources & evidence

ORD record
ord-bc040782250c44ce86d733f8f811d42c
Source dataset
uspto-grants-1997_01
Patent number
US05595686

Reaction notes

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