Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

HRID 1960037Notes

Reaction equation

HRID 1960037 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][CH:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1)=O)C>C1COCC1>[O:17]1[C:16]2([CH2:21][CH2:22][CH:13]([CH2:12][CH2:10][OH:9])[CH2:14][CH2:15]2)[O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-olYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (42.5 g, 1.12 mol) in THF (1200 mL) is carefully added crude 8-ethoxycarbonylmethyl-1,4-dioxaspiro[4.5]decane (174.7 g) in THF solution (640 mL) at 0° C. under argon atmosphere. After stirring for 10 min at ambient temperature, Na2SO4-10H2O (360.9 g) is added at 0° C., and the mixture is stirred for additional 3 hours. Insoluble matter is filtered and washed with EtOAc, and the filtrate is concentrated in vacuo to afford crude 2-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol (139.5 g). The crude product is used without further purification.

Workup

  1. stirringthe mixture is stirred for additional 3 hours
  2. filtrationInsoluble matter is filtered
  3. washwashed with EtOAc
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-d6232f01dcb74fb3a60fe58f0cf2c179
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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