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

HRID 574951

反応式

HRID 574951 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a2d6df101f984777b0639d5917c0bd8f
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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