1,2-Dichloroethane → (2S)-2-[(benzyloxy)methyl]-1,4-dioxane

HRID 222276Notes

Reaction equation

HRID 222276 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:17][CH2:18]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:11][O:12][CH2:18][CH2:17][O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 111,2-Dichloroethane3×HCID 14798Sodium Hydroxide2×HCID 2724795(R)-3-(benzyloxy)propane-1,2-diol

Product 1

HCID 66971993(2S)-2-[(benzyloxy)methyl]-1,4-dioxane

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

(2R)-3-(benzyloxy)propane-1,2-diol (2.00 g, 11.0 mmol) and tetrabutylammonium bromide (708 mg, 2.20 mmol) were dissolved in 50 mL of 1,2-dichloroethane, then 50 mL of a 50% (w/w) aqueous sodium hydroxide solution was added quickly and the mixture was heated to 50° C. After 18 h, an additional 50 mL of 1,2-dichloroethane and 50 mL of 50% (w/w) sodium hydroxide solution was added. After 8 h, additional 50 mL of 1,2-dichloroethane was added. After 72 h, the mixture was diluted in diethyl ether, washed with water and brine, then dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (silica, ethylacetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 7.26-7.35 (m, 5H); 4.51-4.56 (m, 2H); 3.72-3.82 (m, 4H); 3.67-3.71 (m, 1H); 3.58-3.64 (m, 1H); 3.38-3.48 (m, 3H).

Workup

  1. waitAfter 8 h
  2. waitAfter 72 h
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, ethylacetate/hexanes)

Sources & evidence

ORD record
ord-67d48dfdd5914f64b47bbd8dc9dcd20a
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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