Methyl iodide → Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 574950

反応式

HRID 574950 の反応式
[CH:1](NC(C)C)(C)C.[Li]CCCC.[O:13]1[C:17]2([CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.CI>O1CCCC1.O>[CH3:1][C:20]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Into a 500 mL round-bottomed flask was added diisopropylamine (7.98 mL) in tetrahydrofuran (233 mL) to give a colorless solution. The mixture was cooled to −78° C. under N2 and n-BuLi (2.5 M in hexanes, 22.40 mL) was added. The reaction was stirred for 30 minutes and ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (10 g) was added. The reaction was allowed to stir for 1.5 hours upon which time CH3I (4.38 mL) was added. The reaction was allowed to warm to room temperature overnight with stirring. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate).

後処理

  1. customto give a colorless solution
  2. additionwas added
  3. temperatureto warm to room temperature overnight
  4. stirringwith stirring
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organics were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-db027b31eeec4e5c99c853a29ea59b36
出典データセット
uspto-grants-2015_05
特許番号
US09034875B2

関連ノート

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