Ethylene Glycol → 2-Bromo-5,8-dioxaspiro[3.4]octane

HRID 2095710Notes

Reaction equation

HRID 2095710 reaction equation
[Br:1][CH:2]1[CH2:5][C:4](=[O:6])[CH2:3]1.[CH2:7](O)[CH2:8][OH:9].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1C=CC=CC=1>[Br:1][CH:2]1[CH2:5][C:4]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 583469633-Bromocyclobutanone

Product 1

HCID 670043162-Bromo-5,8-dioxaspiro[3.4]octaneYield 51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-bromocyclobutanone (5.90 g, 39.6 mmol), 1,2-ethanediol (8.6 mL, 158 mmol, 4 eq.) and PPTS (1.90 g, 7.92 mmol) in benzene (40 mL) was heated to reflux using Dean-Stark assembly. After 12 h, the reaction mixture was allowed to cool and washed with water (2×30 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified using column chromatography (ethyl acetate/hexanes 1:5) to give the title compound (51% yield starting from 3-oxocyclobutanecarboxylic acid). 1H NMR (300 MHz, CDCl3): δ=2.77-2.82 (m, 4H), 2.95-3.00 (m, 4H), 4.19-4.23 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto cool
  4. washwashed with water (2×30 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-5977d33cd24b4290b3e8d1882c7c5e02
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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