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

HRID 1486209Notes

Reaction equation

HRID 1486209 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12](OCC)=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]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 102.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate from Step 1 (3.31 g, 14.5 mmol) in Et2O (80 mL) at 0° C. under N2 was added LiAlH4 (1M in THF, 13.66 mL, 13.66 mmol) in 15 min. The resulting mixture was stirred at 0° C. for another 20 min and quenched by addition of saturated aqueous NH4Cl solution, extracted with EtOAc, dried over Na2SO4. Filtration and evaporation to dryness gave the alcohol as white solid (2.76 g, 100%). LC/MC: 187.1 (MH)+.

Workup

  1. customquenched by addition of saturated aqueous NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-65666dd26ac04c008e6afdb8d04eb389
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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