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

HRID 1366347Notes

Reaction equation

HRID 1366347 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-aa37bea96fbe49a3bfeece8564a61d37
Source dataset
uspto-grants-2011_02
Patent number
US07893081B2

Reaction notes

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