Water → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

HRID 45011

反応式

HRID 45011 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12](OCC)=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[AlH4-].[Li+].O.[OH-].[Na+]>CCOCC>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

生成物 1

HCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

Ethyl 1,4-dioxaspiro[4.5]dec-8-ylacetate (3.40 g, 0.0149 mol) prepared according to the procedure of Itagaki, Noriaki; Kimura, Mari; Sugahara, Tsutomu; Iwabuchi, Yoshiharu. (Organic Letters 2005; 7 (19); 4181-4183.) was dissolved in ether (30.00 mL) and the mixture was cooled to 0° C. To the reaction was added 1.00 M lithium tetrahydroaluminate in ether (15.0 mL) and the resulting mixture was stirred at 0° C. for 60 minutes and at 25° C. for 2 hours. The reaction was cooled and water (0.40 mL, 0.022 mol) was added, followed by 1.00 M sodium hydroxide (0.40 mL). To the reaction was then added ether (100.00 mL) and the solid that precipitated was filtered off. The filtrate was concentrated using a rotary evaporator to give the product. 1H NMR(CDCl3): 3.94 (s, 4H), 3.67 (t, 2H), 1.20-1.80 (m, 11H).

後処理

  1. temperatureThe reaction was cooled
  2. customadded ether (100.00 mL) and the solid that precipitated
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated
  5. customa rotary evaporator
  6. customto give the product

出典と根拠

ORDレコード
ord-47e94b84837947adb73e56dbada29f69
出典データセット
uspto-grants-2013_09
特許番号
US08541425B2

関連ノート

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