Methyl iodide → HCID 66762091, compound

HRID 561781Notes

Reaction equation

HRID 561781 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].I[CH3:21]>C1COCC1>[Cl:3][C:4]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][CH3:21])=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66761548HCID 66761548, compound

Product 1

HCID 66762091HCID 66762091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% w/w dispersion in oil, 2 eq.) in anhydrous THF (0.23 M) was added tert-butyl 2-chloro-5-(2-hydroxyethyl)benzoate from the previous step (1 eq.). The reaction mixture was heated at reflux for 30 min before iodomethane (7.9 eq.) was added. After carefully quenching with sat. aq. NaHCO3, the resulting mixture was extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added
  3. customAfter carefully quenching with sat. aq. NaHCO3
  4. extractionthe resulting mixture was extracted with ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a cloudy oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-25ba587f4633400eae5dbee9a156fb76
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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