Methyl iodide → HCID 54508541, compound

HRID 259208Notes

Reaction equation

HRID 259208 reaction equation
[OH:1][C:2]([CH3:25])([CH2:20][CH2:21][O:22][CH2:23][CH3:24])[CH:3]=[CH:4][CH:5]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][CH2:6]1.[OH-].[Na+].[CH3:28]I>CN(P(N(C)C)(N(C)C)=O)C>[OH:1][C:2]([CH3:25])([CH2:20][CH2:21][O:22][CH2:23][CH3:24])[CH:3]=[CH:4][CH:5]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:28])=[O:17])[C:8](=[O:19])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 54402081HCID 54402081, compound

Product 1

HCID 54508541HCID 54508541, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

7-[5-(3-Hydroxy-3-methyl-5-ethoxypent-1-enyl)-2-oxocyclopentyl]heptanoic acid (0.24 g.) was diluted with hexamethylphosphotriamide (1.8 ml.) and treated with aqueous sodium hydroxide solution (25% w/v; 0.163 ml.). After stirring for two hours at room temperature, methyl iodide (0.177 ml.) was added and stirring continued for a further 24 hours. The reaction mixture was extracted twice with diethyl ether and the combined ethereal extracts were washed twice with water and dried over anhydrous sodium sulphate. Evaporation gave crude methyl 7-[5-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-2-oxocyclopentyl]heptanoate (0.17 g.) as the residue. This was purified by preparative thin-layer chromatography on silica gel, using mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant, to give methyl 7-[5-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-2-oxocyclopentyl]-heptanoate (30 mg.). Elemental analysis: found: C, 68.3; H, 10.1%; C21H36O5 requires: C, 68.5; H, 9.9%. N.M.R. (approximately 10% solution in deuterochloroform): triplet at 1.2δ (J=7 cycles/sec.), singlet at 1.3δ, multiplets at 1.0-2.0δ, 2.0-2.5δ, 3.2-3.75δ, singlet at 3.6δ, and multiplet at 5.6-5.8δ.

Workup

  1. stirringstirring
  2. waitcontinued for a further 24 hours
  3. extractionThe reaction mixture was extracted twice with diethyl ether
  4. washthe combined ethereal extracts were washed twice with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customEvaporation
  7. customgave crude methyl 7-[5-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-2-oxocyclopentyl]heptanoate (0.17 g.) as the residue
  8. customThis was purified by preparative thin-layer chromatography on silica gel
  9. additionmixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant

Sources & evidence

ORD record
ord-50f9652c884349938865dc522a5374fc
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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