Methyl 1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate → 1,4-Dioxaspiro[4.5]dec-7-en-8-ylmethanol

HRID 1741027Notes

Reaction equation

HRID 1741027 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]1

Participants

4

Reactant 2

HCID 12563052Methyl 1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 109649381,4-Dioxaspiro[4.5]dec-7-en-8-ylmethanolYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. additionwas added dropwise
  2. customquenched by successive addition of methanol (9 ml), ethanol (9 ml) and water (9 ml)
  3. additionThe gelatinous mixture was diluted with ethyl acetate
  4. filtrationfiltered through kieselguhr
  5. washThe filtrate was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c582ef55e69146c5863d9781f971aeaa
Source dataset
uspto-grants-1999_10
Patent number
US05972979

Reaction notes

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