Methyl iodide → HCID 59267933, compound

HRID 553635Notes

Reaction equation

HRID 553635 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])[CH3:4].I[CH3:16]>C1COCC1>[CH2:3]([O:5][C:6]([C:8]1([CH2:13][O:14][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46172884HCID 46172884, compound

Product 1

HCID 59267933HCID 59267933, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride in mineral oil (6.2 g, 130.8 mmol) is added to a solution of 1-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (15.0 g, 87.2 mmol) in 100.0 mL of THF at 0° C., followed by the addition of iodomethane (13.6 g, 95.9 mmol) and the reaction mixture is stirred at room temperature for 14 hours. After this time, the reaction mixture is quenched with ice water and then extracted with ethyl acetate twice. The organics are combined and washed with water twice then brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product that is purified by silica gel chromatography to afford 12.0 g of the title compound. Yield: 74%; m/z 209 [M+Na].

Workup

  1. customAfter this time, the reaction mixture is quenched with ice water
  2. extractionextracted with ethyl acetate twice
  3. washwashed with water twice
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product that
  8. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-01f744fe3f2c4cd4b70587af1a6528ed
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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