Ethyl 4-hydroxycyclohexanecarboxylate → HCID 89582057, compound

HRID 1482876Notes

Reaction equation

HRID 1482876 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[OH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1>CN(C=O)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:9][CH:10]2[CH2:11][CH2:12][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15]2)=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 89582057HCID 89582057, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-bromo-2-chloro pyrimidine (1.00 g, 5.17 mmol) and ethyl 4-hydroxycyclohexanoate (0.834 mL, 5.17 mmol) in DMF (20 mL) was added sodium hydride NaH (60% weight in mineral oil, 0.227 g, 5.69 mmol). The reaction mixture was stirred for 16 hours before being diluted with saturated aqueous sodium bicarbonate (50 mL), ethyl acetate (50 mL), and diethyl ether (50 mL). The layers were separated and the organic layer was washed with water (3×50 mL) and then brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/hexanes) to yield ethyl 4-[(5-bromopyrimidin-2-yl)oxy]cyclohexanecarboxylate as a mixture of cis and trans isomers. MS ESI calc'd. for C13H18BrN2O3 [M+H]+ 329 and 331. found 329 and 331.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water (3×50 mL)
  3. dry with materialbrine (50 mL), dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b836ec9251984575aaa4e778034e3818
Source dataset
uspto-grants-2016_08
Patent number
US09416111B2

Reaction notes

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