Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate → 1,4-Dioxaspiro[4.5]decan-8-ylmethanol

HRID 1960025Notes

Reaction equation

HRID 1960025 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1)=O)C>C1COCC1>[O:16]1[C:15]2([CH2:20][CH2:21][CH:12]([CH2:10][OH:9])[CH2:13][CH2:14]2)[O:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (50.5 g, 1.06 mol) in THF (800 mL) is carefully added crude 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (220 g) in THF (700 mL) at 0° C. over 2.5 hours under argon atmosphere. After stirring 1 hour at ambient temperature, Na2SO4-10H2O (175 g) is added at 0° C., and the mixture is stirred for additional 10 min. Insoluble matter is filtered, and the filtrate is concentrated in vacuo to afford crude (1,4-dioxa-spiro[4.5]dec-8-yl)methanol as a colorless oil, which is used without further purification.

Workup

  1. stirringthe mixture is stirred for additional 10 min
  2. filtrationInsoluble matter is filtered
  3. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-e77e085bee5640fbb3bcd5ee2350ab08
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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