Benzyl Bromide → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

HRID 1970980Notes

Reaction equation

HRID 1970980 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[CH2:14]([O: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:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of NaH (60%, 4.05 g, 101 mmol) in DMF (50 mL) was added 1,4-dioxaspiro[4.5]decan-8-ol (10 g, 63 mmol) dropwise at 0° C. The reaction mixture was allowed to warm to room temperature, and treated with benzyl bromide (9.02 mL, 76 mmol). The mixture was heated to 50° C. overnight, diluted with EtOAc, and washed with water (×5). The organic layer was dried, concentrated, and purified by flash chromatography to afford the title compound.

Workup

  1. temperatureThe mixture was heated to 50° C. overnight
  2. washwashed with water (×5)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-51ae688c7690411ab710e07dd1ced328
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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