Methyl iodide → HCID 86691238, compound

HRID 2038221Notes

Reaction equation

HRID 2038221 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:17]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH2:10][O:11][CH3:17])[CH2:8][OH:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86691236HCID 86691236, compound

Product 1

HCID 86691238HCID 86691238, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-(4-fluorophenoxy)propane-1,3-diol (186 mg, 0.99 mmol) in THF (5 mL), and add sodium hydride (60% dispersion in mineral oil, 24 mg, 1 mmol). Stir the mixture for 30 minutes at ambient temperature then add iodomethane (0.4 mL, 4.09 mmol). Stir the reaction at ambient temperature for 16 hours. Remove the solvents under reduced pressure and add water to the residue. Extract with EtOAc three times; collect the EtOAc extracts; dry; and remove the solvents under reduced pressure. Purify the residue via prep-TLC using 1:1 EtOAc:petroleum ether, to give the title compound (50 mg, 31.0%). 1H NMR (300 MHz, CDCl3) δ 7.0 (m, 4H), 4.2-4.5 (m, 2H), 3.8 (m, 2H), 3.55 (m, 1H), 3.35 (m, 2H), 2.35 (bs, 1H), 2.0 (s, 3H).

Workup

  1. stirringStir
  2. customthe reaction at ambient temperature for 16 hours
  3. customRemove the solvents under reduced pressure
  4. additionadd water to the residue
  5. extractionExtract with EtOAc three times
  6. customcollect the EtOAc
  7. customdry
  8. customand remove the solvents under reduced pressure
  9. customPurify the residue

Sources & evidence

ORD record
ord-10b40c8b93d2451ea35ebc5260a8d0f8
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

Loading…