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

HRID 511393ノート

反応式

HRID 511393 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-2df7781d5a694dc9a9419684deeef762
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

反応ノート

読み込み中…