Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → (8-Methyl-1,4-dioxaspiro[4.5]decan-8-yl)methanol

HRID 574951

반응식

HRID 574951 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([C:18](OCC)=[O:19])[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1>O1CCCC1>[CH3:7][C:8]1([CH2:18][OH:19])[CH2:17][CH2:16][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:10][CH2:9]1

참가 물질

4

반응물 2

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 12568263(8-Methyl-1,4-dioxaspiro[4.5]decan-8-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

In a 500 ml, round-bottomed flask was lithium aluminum hydride (1.772 g) in tetrahydrofuran (234 mL) to give a suspension. This suspension was cooled to 0° C. and ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (10.66 g) was added via addition funnel. The reaction was stirred overnight at room temperature and then cooled back down to 0° C. The excess lithium aluminum hydride was slowly quenched with 1.8 mL water, 1.8 mL aqueous NaOH (5N) and 5.6 mL water. The suspension was stirred until the salts turned white and was then filtered through a plug of silica gel. The filtrate was concentrated by rotary evaporation and the residue was purified by regular phase flash column chromatography (Analogix, 0-75% hexanes/ethyl acetate).

후처리

  1. customto give a suspension
  2. temperaturecooled back down to 0° C
  3. customThe excess lithium aluminum hydride was slowly quenched with 1.8 mL water, 1.8 mL aqueous NaOH (5N) and 5.6 mL water
  4. stirringThe suspension was stirred until the salts
  5. filtrationwas then filtered through a plug of silica gel
  6. concentrationThe filtrate was concentrated by rotary evaporation
  7. customthe residue was purified by regular phase flash column chromatography (Analogix, 0-75% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-a2d6df101f984777b0639d5917c0bd8f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034875B2

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