Water → O-Benzyl-3,6,9-trioxacyclodecan-1-ol

HRID 1889131Notes

Reaction equation

HRID 1889131 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[CH2:3]([O:10][CH:11]1[CH2:12][O:13][CH2:17][CH2:21][O:20][CH2:19][CH2:18][O:15][CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 2035672-(Phenylmethoxy)-1,3-propanediol

Product 1

HCID 25129101O-Benzyl-3,6,9-trioxacyclodecan-1-olYield 19%

Conditions

Temperature
23 °C

Procedure

To a refluxing suspension of sodium hydride (60% in mineral oil, pre-washed with hexane, 84 mg, 2.1 mmol) in dry THF (5 mL), a solution of 17 (182 mg, 1.0 mmol) and di(ethyleneglycol)dimethanesulfonate (260 mg, 1.0 mmol) in dry THF (5 mL) was added dropwise. The resulting mixture was heated under reflux for 20 h, afterward was cooled to 23° C. and H2O (2 mL) was added. The solvent was removed and the aqueous phase was extracted with CHCl3. The organic extracts were washed several times with water, dried (Na2SO4) and evaporated. The residue was purified by flash-chromatography (2:3 CH2Cl2/EtOAc) to afford 49 mg (19%) of 18 as a colourless oil: 1H NMR (CDCl3) δ 7.36-7.26 (m, 5H), 4.66 (s, 2H), 3.75-3.57 (m, 13H); MS (ESI) m/z 275 [M+Na]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 20 h
  3. customThe solvent was removed
  4. extractionthe aqueous phase was extracted with CHCl3
  5. washThe organic extracts were washed several times with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by flash-chromatography (2:3 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-343ea7201a7a4a7c8d890bdce9d0e390
Source dataset
uspto-grants-2013_08
Patent number
US08501961B2

Reaction notes

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