Lithium aluminum hydride → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 40985

Reaction equation

HRID 40985 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[AlH4-].[Li+]>CCOCC>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

1,4-Dioxa-spiro[4.5]decan-8-one (2.00 g, 0.0128 mol) was dissolved in ether (50 mL) and the mixture was cooled to 0° C. To the reaction was added 1 M lithium tetrahydroaluminate in ether (7.0 mL) and this mixture was stirred at 0° C. for 2 hours at which time TLC analysis showed no starting material present. The reaction was then quenched with water and 1 N NaOH (0.5 mL of each) and then filtered. The filtered solid was washed with ether and the combined ether filtrate was concentrated using a rotary evaporator to give the product. NMR (CDCl3): 3.94 (m, 4H), 3.81 (m, 1H), 1.79-1.92 (m, 4H), 1.54-1.70 (m, 4H).

Workup

  1. customThe reaction was then quenched with water and 1 N NaOH (0.5 mL of each) and
  2. filtrationthen filtered
  3. washThe filtered solid was washed with ether
  4. concentrationthe combined ether filtrate was concentrated
  5. customa rotary evaporator
  6. customto give the product

Sources & evidence

ORD record
ord-5c426494f53b403092b47b43b4284363
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Linked notes

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