Water → 1,4-Dioxaspiro[4.5]decan-6-ylmethanol

HRID 73623Notes

Reaction equation

HRID 73623 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11](OC)=[O:12])[O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[CH2:11][OH:12])[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12869104Methyl 1,4-dioxaspiro[4.5]decane-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 40665581,4-Dioxaspiro[4.5]decan-6-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate (3.00 g, 15.0 mmol) in THF (45 mL) at 0° C. was added LiAlH4 (2M in TI-IF (9.00 mL, 18.0 mmol) dropwise. The mixture was then allowed to warm to rt and stirred overnight. The mixture was then cooled to 0° C. and 1.36 mL of H2O was added very slowly. The reaction mixture was basified by adding 0.682 mL of 15% NaOH and then 3.41 mL of H2O. The resulting mixture was filtered through a pad of celite, washed with Et2O, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.95-4.05 (m, 4H), 3.71-3.79 (m, 1H), 3.52-3.59 (m, 1H), 2.81 (dd, 1H, J=3.9 Hz, 7.1 Hz), 1.78-1.91 (m, 2H), 1.61-1.73 (m, 3H), 1.41-1.53 (m, 2H), 1.24-1.40 (m, 2H).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationThe resulting mixture was filtered through a pad of celite
  3. washwashed with Et2O
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d1f35abc157744969a1e311e7a4e3b05
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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