Methyl iodide → HCID 178501285, compound

HRID 2091981Notes

Reaction equation

HRID 2091981 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[C:11]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.CCOC(C)=O>[CH3:11][O:9][C:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]1)=[O:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178525780HCID 178525780, compound

Product 1

HCID 178501285HCID 178501285, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-4-hydroxycyclohexanecarboxylic acid (14.7 mmol, 2.12 g), K2CO3 (17.6 mmol, 2.44 g) in DMF (15 mL) is added iodomethane (17.6 mmol, 1.10 mL). After stirring for 2 hours, the mixture is diluted with EtOAc. The mixture is washed with H2O and brine, dried over Na2SO4 and concentrated. The obtained residue is used to next reaction without further purification (1.62 g, 70%); 1H-NMR (400 MHz, CDCl3): 1.24-1.33 (m, 2H), 1.45-1.53 (m, 2H), 1.98-2.28 (m, 4H), 2.21-2.29 (m, 1H), 3.57-3.64 (m, 1H), 3.67 (s, 3H).

Workup

  1. washThe mixture is washed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe obtained residue is used to next reaction without further purification (1.62 g, 70%)

Sources & evidence

ORD record
ord-b858146a9a2d4248b2f9917cf601da6a
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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