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

HRID 1036038Notes

Reaction equation

HRID 1036038 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 dropwise a solution of EXAMPLE 341A (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 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 was 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 sodium hydroxide (8 mL), ether (200 mL), water (24 mL), ether (500 mL) and anhydrous sodium sulfate (250 g)
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-1b07e29859604fdba962f9ac1a6257b6
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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