Methyl iodide → HCID 22915168, compound

HRID 1377593Notes

Reaction equation

HRID 1377593 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([C:18]2([OH:23])[CH2:22][O:21][CH2:20][CH2:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:24]I>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([C:18]2([O:23][CH3:24])[CH2:22][O:21][CH2:20][CH2:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22915174HCID 22915174, compound

Product 1

HCID 22915168HCID 22915168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% w/w dispersion in mineral oil, 1.3 g) was added to a solution of 4-(3-benzyloxy-5-fluorophenyl)-4-hydroxytetrahydrofuran (9.1 g) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for about 1 hour then cooled to about 0° C. with an ice-bath. Methyl iodide (4 ml) was added and the mixture stirred at room temperature for about 20 hours. The mixture was quenched with aqueous 10% hydrochloric acid (1 ml) and the tetrahydrofuran was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was separated, dried over sodium sulfate and evaporated to give 5.9 g of the title compound as an oil.

Workup

  1. temperaturethen cooled to about 0° C. with an ice-bath
  2. stirringthe mixture stirred at room temperature for about 20 hours
  3. customThe mixture was quenched with aqueous 10% hydrochloric acid (1 ml)
  4. customthe tetrahydrofuran was evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. customThe organic phase was separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0cb393896e2e4d45a126da4d7ae75b46
Source dataset
uspto-grants-1997_09
Patent number
US05665749

Reaction notes

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