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

HRID 2045116Notes

Reaction equation

HRID 2045116 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([C:17](OCC)=[O:18])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1>O1CCCC1>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]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 suspension of lithium aluminum hydride (8.19 g) in tetrahydrofuran (400 mL) was added slowly dropwise a solution of EXAMPLE 531A (37.8 g) in tetrahydrofuran (75 mL). The mixture was then heated at reflux for 2 hours. The reaction mixture was cooled in an ice bath and quenched very slowly with water (8 mL). Then added sequentially were 4N aqueous sodium hydroxide (8 mL), ether (200 mL), water (24 mL), ether (500 mL) and anhydrous sodium sulfate (250 g). The resulting mixture was stirred rapidly for 2 hours and then filtered. The title compound was isolated by concentration of the filtrate.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customquenched very slowly with water (8 mL)
  5. additionThen added sequentially were 4N aqueous sodium hydroxide (8 mL), ether (200 mL), water (24 mL), ether (500 mL) and anhydrous sodium sulfate (250 g)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2c37510fc9494e6ea763997546d1d91d
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

Loading…