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

HRID 1789562노트

반응식

HRID 1789562 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-84333a5b19d34faba23cff08212dd607
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04689345

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