Benzyl Bromide → 6-((Benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane

HRID 1748170Notes

Reaction equation

HRID 1748170 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[CH2:11][OH:12])[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.C(OCC)(=O)C>[CH2:15]([O:12][CH2:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]21[O:4][CH2:3][CH2:2][O:1]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 40665581,4-Dioxaspiro[4.5]decan-6-ylmethanol

Product 1

HCID 686237586-((Benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,4-dioxaspiro[4.5]decan-6-ylmethanol (2.3 g, 13.3 mmol) in THF (20 mL) and cooled in an ice bath, was treated with a NaH (0.48 g, 20.0 mmol). The reaction mixture was stirred for 1 hour and then benzyl bromide (2.4 mL, 20 mmol) in THF (5 mL) was added dropwise. The reaction was stirred at rt for 5 hours and then diluted with ethyl acetate (100 mL). The organic layer was washed with water, brine and dried over sodium sulfate and concentarted. Purification by silica chromatography using hexane-Et2O 20% linear gradient afforded the title compound as pale yellow solid. MS m/z 263.2 (M+1).

Workup

  1. stirringThe reaction was stirred at rt for 5 hours
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customPurification by silica chromatography

Sources & evidence

ORD record
ord-93c2edb9ff474664b4057c2f21984b13
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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