Methyl iodide → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether

HRID 273737Notes

Reaction equation

HRID 273737 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([OH:20])[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.I[CH3:22]>C1COCC1>[CH3:22][O:20][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:11][CH2:12][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 152326818-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 571381988-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl etherYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (1.27 g, 31.7 mmole) was added to a solution of 8-(4-fluoro-phenyl)-1,4-dioxaspiro[4.5]decan-8-ol (8.0 g, 10 mmole) in THF (100 ml) and the mixture stirred for 16 hr and heated at reflux for 4 hr. The solution was cooled to 25° C. and iodomethane (6.75 g, 47.6 mmole) was added. The mixture was stirred for 112 hr and concentrated in vacuo. The residue was suspended in water and the mixture extracted with methylene chloride. The extracts were dried and concentrated in vacuo to give 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether (98.8%, mp: 52°-54° C.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hr
  3. stirringThe mixture was stirred for 112 hr
  4. concentrationconcentrated in vacuo
  5. extractionthe mixture extracted with methylene chloride
  6. customThe extracts were dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7f1748a0d014cf582b5653dfe57861f
Source dataset
uspto-grants-1995_02
Patent number
US05387593

Reaction notes

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