Sodium Iodide → 3-t-Butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane)
Reaction equation
CS(O)(=O)=O.[C:6]([C:10]1([CH2:18]O)[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7].[I-:20].[Na+].[C:22]1(=O)[CH2:27]CCC[CH2:23]1>>[C:6]([C:10]1([CH2:18][I:20])[CH2:11][O:12][C:13]2([CH2:16][CH2:27][CH2:22][CH2:23][CH2:17]2)[O:14][CH2:15]1)([CH3:7])([CH3:8])[CH3:9]Participants
Procedure
A mixture of cyclohexanone (150 ml.), 5-t-butyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane methanesulphonate (17.5 g.) (see synthesis of 2,2-dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methanesulphonate and ref. 4) and sodium iodide (12 g.) was refluxed, with stirring, for 24 hours. The solvent was removed in vacuo and the resulting oil was poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with 5% aqueous sodium thiosulphate solution and then water. The ethereal extracts were dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with hexane. 3-t-Butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane) was obtained as a colourless oil (14 g.) Gas-liquid chromatography (g.l.c.): OV210 at 185° produced one peak.
Workup
- temperaturewas refluxed
- customThe solvent was removed in vacuo
- additionthe resulting oil was poured into water
- extractionThe aqueous mixture was extracted with diethyl ether
- washThe ethereal extracts were washed with 5% aqueous sodium thiosulphate solution
- dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica
- washeluting with hexane
Sources & evidence
- ORD record
- ord-7ba1cedc02f64d788063b50ae74cb1a8
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04985582
Reaction notes
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