Sodium Iodide → 3-t-Butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane)

HRID 704135ノート

反応式

HRID 704135 の反応式
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]

参加物

4

反応物 3

HCID 5238Sodium IodideHCID 7967CyclohexanoneHCID 867445215-t-Butyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane methanesulphonate

生成物 1

HCID 200756033-t-Butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane)

実験手順

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.

後処理

  1. temperaturewas refluxed
  2. customThe solvent was removed in vacuo
  3. additionthe resulting oil was poured into water
  4. extractionThe aqueous mixture was extracted with diethyl ether
  5. washThe ethereal extracts were washed with 5% aqueous sodium thiosulphate solution
  6. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica
  9. washeluting with hexane

出典と根拠

ORDレコード
ord-7ba1cedc02f64d788063b50ae74cb1a8
出典データセット
uspto-grants-1991_01
特許番号
US04985582

反応ノート

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