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

HRID 2168118Notes

Reaction equation

HRID 2168118 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-42a2803f7d16412eab41e15c64846219
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

Loading…