Methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate → 1,4-Dioxaspiro[4.5]decan-6-ylmethanol

HRID 1748169Notes

Reaction equation

HRID 1748169 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]>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

4

Reactant 2

HCID 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 solution of methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate (3.87 g, 19.3 mmol) in THF (40 mL) and cooled to 0°C. LiAlH4 was added dropwise and stirred for 5 hours. The reaction was quenched by subsequent dropwise addition of water (1.3 mL) 15% NaOH (1.3 mL) and water (2.6 mL) and filtered thru a CELITE® pad. Concentration of the filtrate afforded the title compound as clear oil that was carried to the next step without further purification. MS m/z 173.1 (M+1).

Workup

  1. customThe reaction was quenched by subsequent dropwise addition of water (1.3 mL) 15% NaOH (1.3 mL) and water (2.6 mL)
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8107b88cb0234f85a70d37519f0a583a
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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