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

HRID 1501481Notes

Reaction equation

HRID 1501481 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a7f23ee9bc57414d9de0e8fe743c398f
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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