Lithium aluminum hydride → 1,4-Dioxaspiro(4.5)decan-8-ol
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was then quenched with water and 1 N NaOH (0.5 mL of each) and
- filtrationthen filtered
- washThe filtered solid was washed with ether
- concentrationthe combined ether filtrate was concentrated
- customa rotary evaporator
- customto give the product
Sources & evidence
- ORD record
- ord-56b70c60c9bd483d8416b2cb3a87ec37
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079912B2
Reaction notes
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