Cyclopentanol → HCID 21187847, compound

HRID 356966Notes

Reaction equation

HRID 356966 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:25]=1[O:26][C:27]([F:30])([F:29])[F:28])[C:19]([O:21][CH3:22])=[O:20].[CH:31]1(O)[CH2:35][CH2:34][CH2:33][CH2:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:31]1([O:15][C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][C:25]=2[O:26][C:27]([F:28])([F:29])[F:30])[C:19]([O:21][CH3:22])=[O:20])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21187932HCID 21187932, compound

Product 1

HCID 21187847HCID 21187847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.61 mL) is added to a solution of methyl 3-hydroxy-4-trifluoromethoxybenzoate (0.74 g), cyclopentanol (0.19 g) and triphenylphosphine (0.81 g) in tetrahydrofuran (10 mL) and the mixture is heated overnight at reflux. Solvent is evaporated off under reduced pressure and the resulting yellow oil is triturated with diethyl ether. The white solid thus formed is filtered off, and the filtrate is evaporated under reduced pressure and subjected to mplc, to give methyl 3-cyclopentyloxy-4-trifluoromethoxy-benzoate in the form of a pale yellow oil (0.6 g).

Workup

  1. temperaturethe mixture is heated overnight
  2. temperatureat reflux
  3. customSolvent is evaporated off under reduced pressure
  4. customthe resulting yellow oil is triturated with diethyl ether
  5. customThe white solid thus formed
  6. filtrationis filtered off
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e380c933a3384f79bd9b505b5f01f7b3
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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