Methyl 1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate → 1,4-Dioxaspiro[4.5]dec-7-en-8-ylmethanol
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11](OC)=[O:12])=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([CH2:11][OH:12])=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 1,4-dioxaspiro[4,5]dec-7-ene-8-carboxylate [J. Org. Chem. 40, 538 (1975)] (1.00 g, 5.0 mmol) was stirred under Ar in dry THF (50 ml) at -78° C. as diisobutylaluminium hydride (1.5M in toluene, 8.4 ml, 12.6 mmol) was added dropwise. The mixture was stirred, warming to ambient temperature, for 2.5 h, and then quenched by successive addition of methanol (9 ml), ethanol (9 ml) and water (9 ml). The gelatinous mixture was diluted with ethyl acetate, and filtered through kieselguhr. The filtrate was washed with brine, dried (Na2SO4) and evaporated to give the title compound (0.79 g, 92%) as a colourless oil.