Cyclopentanemethanol → 426829-74-5

HRID 1357594Notes

Reaction equation

HRID 1357594 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11](Cl)[N:10]=1>O1CCOCC1.ClCCl.CCOCC>[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:10]=1

Participants

5

Reactant 2

HCID 77195CyclopentanemethanolHCID 785042,6-Dichloropyrazine

Product 1

HCID 18186863426829-74-5Yield 61%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

K-t-BuO (1.65 g, 14.7 mmol) was added portionwise to a stirred mixture of cyclopentanemethanol (2.99 g, 29.9 mmol) and 2,6-dichloropyrazine (1.90 g, 12.8 mmol) in dioxane (6 mL) at 0° C. (ice-bath). The reaction mixture was then stirred for 2.5 h, while the temperature was allowed to reach room temperature. The reaction mixture was diluted with dichloromethane/ether (1:1), filtered, and concentated in vacuo. The beige liquid was purified by column chromatography on silica gel (18×4 cm) using n-hexane/ethyl acetate (94:6) as eluent. Two chromatographic runs afforded 1.66 g (61%) of the title compound as a colorless oil. HRMS m/z calcd for C10H13ClN2O (M)+212.0716, found 212.0723. Anal. (C10H13ClN2O) C, H, N.

Workup

  1. customto reach room temperature
  2. filtrationfiltered
  3. customThe beige liquid was purified by column chromatography on silica gel (18×4 cm)

Sources & evidence

ORD record
ord-8645b595c8f546ceb0d2a821900d9aaa
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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