Sodium Iodide → 7-Methoxy-2-(5-methoxyhept-1-y)bicyclo[3.3.0]octane

HRID 1789562ノート

反応式

HRID 1789562 の反応式
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][CH:11]([OH:16])[CH2:12]2.[I-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][O:16][CH:11]1[CH2:10][CH:9]2[CH:13]([CH2:14][CH2:15][CH:8]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:17][CH3:18])[CH2:12]1

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 6328Methyl iodideHCID 15053012Octahydro-4-(5-methoxyheptyl)-2-pentalenol

生成物 1

HCID 150530477-Methoxy-2-(5-methoxyhept-1-y)bicyclo[3.3.0]octane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

The starting material, 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]7 octanol {octahydro-4-(5-methoxyheptyl)-2-pentalenol} (1.0 g, 3.9 mmoles) is added to a reaction vessel containing sodium iodide (0.12 g, 4.9 mmoles) and tetrahydrofuran (12 ml). The solution is stirred while methyl iodide (0.84 g, 5.9 mmoles) is rapidly added. The reaction is heated in a 50° C. water bath for 4 hours. The water bath is removed and the reaction neutralized with the addition of water (5 ml). The organic phase is separated and the aqueous phase extracted with ether (2×50 ml). The ether extracts are combined and washed with brine (50 ml). The solution is dried over anhydrous magnesium sulfate and the solvent removed under vacuum leaving a clear yellow oil. The product is then kugelrohred under reduced pressure leaving a pale yellow oil (0.8 g, 3.1 mmoles).

後処理

  1. additionis added to a reaction vessel
  2. additionis rapidly added
  3. customThe water bath is removed
  4. additionthe reaction neutralized with the addition of water (5 ml)
  5. customThe organic phase is separated
  6. extractionthe aqueous phase extracted with ether (2×50 ml)
  7. washwashed with brine (50 ml)
  8. dry with materialThe solution is dried over anhydrous magnesium sulfate
  9. customthe solvent removed under vacuum
  10. customleaving a clear yellow oil

出典と根拠

ORDレコード
ord-84333a5b19d34faba23cff08212dd607
出典データセット
uspto-grants-1987_08
特許番号
US04689345

反応ノート

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