Water → 8-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

HRID 1960038Notes

Reaction equation

HRID 1960038 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[CH2:16]([O:15][CH2:14][CH2:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

Product 1

HCID 218796038-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of NaH (60% in oil, 43.6 g, 1.09 mol) in DMF (900 mL) is carefully added crude 2-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol (139.5 g) in DMF (300 mL) at 0-5° C., and the mixture is stirred for 30 min at the same temperature. To the mixture is added dropwise benzyl bromide (129.6 mL, 1.09 mol) at 0-5° C., and stirring is continued for 1 hour at the same temperature. After addition of H2O (1000 mL), the mixture is extracted with EtOAc-Hexane (3:1, 1200 mL). The water layer is extracted with EtOAc-Hexane (3:1, 1200 mL×2), and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford crude 8-[2-(benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane. The crude product is used without further purification.

Workup

  1. stirringstirring
  2. waitis continued for 1 hour at the same temperature
  3. extractionthe mixture is extracted with EtOAc-Hexane (3:1, 1200 mL)
  4. extractionThe water layer is extracted with EtOAc-Hexane (3:1, 1200 mL×2)
  5. washthe combined organic layer is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee1adc3b5fcb447d8dc19e75c3b6101b
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

Loading…