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

HRID 574950

반응식

HRID 574950 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-db027b31eeec4e5c99c853a29ea59b36
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034875B2

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