Hydrochloric Acid → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

HRID 1631873Notes

Reaction equation

HRID 1631873 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O1CCCC1.O>[CH2:14]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decaneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

1,4-dioxa-spiro[4.5]decan-8-ol (11.0 g, 70 mmol) in dry tetrahydrofuran (50 ml) is added dropwise to a stirred suspension of 60% sodium hydride disperse in mineral oil (2.80 g, 70 mmol) in dry tetrahydrofuran (50 ml). Once the addition is complete the reaction mixture is stirred for 2 hours at room temperature. A solution of benzyl bromide (13.2 g, 77 mmol) in dry tetrahydrofuran (50 ml) is added dropwise over a period of 20 minutes and stirred at room temp overnight. The reaction mixture is poured into water (200 ml), neutralised with 0.5 N aqueous hydrochloric acid and extracted with methylene chloride (2×100 ml). The combined organic layer was dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is absorbed onto silica gel and purified on flash chromatography to give 8-benzyloxy-1,4-dioxa-spiro[4.5]decane (16 g).

Workup

  1. additionOnce the addition
  2. stirringstirred at room temp overnight
  3. extractionextracted with methylene chloride (2×100 ml)
  4. dry with materialThe combined organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue is absorbed onto silica gel
  8. custompurified on flash chromatography

Sources & evidence

ORD record
ord-eee21f4871fb44a3a83b02284838647e
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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