Iodoethane → 8-Ethoxy-1,4-dioxaspiro[4.5]decane

HRID 1947962ノート

反応式

HRID 1947962 の反応式
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:14](I)[CH3:15]>C1COCC1>[CH2:14]([O:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[CH3:15]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

生成物 1

HCID 5673588-Ethoxy-1,4-dioxaspiro[4.5]decane収率 55.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (506 mg, 12.65 mmol) was added to a solution of 1,4-Dioxa-spiro[4.5]decan-8-ol (2 gm, 12.65 mmol) in dry THF (20 mL) at 0° C. After 15 minutes, ethyl iodide (2 gm, 12.65 mmol) was added and the mixture was allowed to stir at RT overnight. After removing the THF under reduced pressure, the mixture was poured into ice cold water and extracted into ethyl acetate. The crude product was purified by flash column chromatography (EtOAc:Hexane 5:95) to isolate the title compound (1.3 gm, 55%). 1H NMR (CDCl3, 500 MHz): δ 1.2 (t, 3H, J=7), 1.45-1.92 (m, 8H), 3.4 (m, 1H), 3.45 (m, 2H), 3.98 (m, 4H).

後処理

  1. customAfter removing the THF under reduced pressure
  2. additionthe mixture was poured into ice cold water
  3. extractionextracted into ethyl acetate
  4. customThe crude product was purified by flash column chromatography (EtOAc:Hexane 5:95)

出典と根拠

ORDレコード
ord-3cd1ad02502040dea7a54b5425ebf52f
出典データセット
uspto-grants-2013_03
特許番号
US08399433B2

反応ノート

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