Cyclohexanol → HCID 86748268, compound

HRID 2380274Notes

Reaction equation

[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](O)[CH:8]=1)([CH3:3])[CH3:2].[CH:19]1(O)[CH2:24][CH2:23][CH2:22]CC1.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:22][CH2:23][CH:24]([CH3:19])[CH3:26])[CH:8]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

2.0 g of 1-(O-isopropyl-3-hydroxybenzohydroximoyl)-1H-1,2,4-triazole, 1.6 g of cyclohexanol, and 4.3 g of triphenylphosphine were dissolved in 100 ml of THF. The mixture was maintained at about 5° C. To the solution was added 10 ml of a THF solution dissolving 2.8 g of diethyl azodicarboxylate drop by drop for 30 minutes. The mixture was stirred for 8 hours at room temperature. The solvent in the resultant mixture was removed under reduced pressure. The residue was purified by column chromatography (eluate: hexane/ethyl acetate=4/1), thus obtaining 2.1 g (yield: 78%) of the desired product (transparent viscous liquid) having a refractive index of [nD20 ] 1.5490 at 20° C.

Workup

customThe solvent in the resultant mixture was removed under reduced pressure
customThe residue was purified by column chromatography (eluate: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-aa3b8f95a315431aa673df70a287640f
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05366988

Reaction notes

Loading…