Tetrahydrofuran → HCID 23116351, compound

HRID 499880Notes

Reaction equation

HRID 499880 reaction equation
C(OCC[C:7]1[C:8]([Br:23])=[C:9]([O:19][CH2:20][O:21][CH3:22])[CH:10]=[C:11]([O:15][CH2:16][O:17][CH3:18])[C:12]=1[CH2:13][CH3:14])C=C.C[N+]1([O-])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.S([O-])([O-])(=[O:34])=S.[Na+].[Na+].[O:39]1[CH2:43]CCC1>O.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[CH3:22][O:21][CH2:20][O:19][C:9]1[C:8]([Br:23])=[C:7]([CH2:26][CH2:27][O:28][CH2:29][CH:30]([OH:34])[CH2:43][OH:39])[C:12]([CH2:13][CH3:14])=[C:11]([O:15][CH2:16][O:17][CH3:18])[CH:10]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23116214HCID 23116214, compound

Product 1

HCID 23116351HCID 23116351, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3-(2-Allyloxyethyl)-1,5-bis(methoxymethoxy)-2-bromo-4-ethylbenzene (5.0 g, 13 mmol) obtained in Example 33, Step 2 was dissolved in a mixed solvent of tetrahydrofuran (50 mL) and water (10 mL). To the solution were added 4-methylmorpholine N-oxide (1.9 g, 16 mmol) and a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (1.0 mL) at room temperature with stirring, and the mixture was stirred overnight. After addition of a saturated aqueous solution of sodium thiosulfate, the reaction mixture was further stirred for 2 hours and then extracted twice with ethyl acetate. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 3-{2-[3,5-bis(methoxymethoxy)-2-bromo-6-ethylphenyl]ethoxy}propane-1,2-diol. The obtained 3-{2-[3,5-bis(methoxymethoxy)-2-bromo-6-ethylphenyl]ethoxy}propane-1,2-diol was dissolved in N,N-dimethylformamide (50 mL), and 2,2-dimethoxypropane (6.4 mL, 52 mmol) and p-toluenesulfonic acid monohydrate (0.12 g, 0.63 mmol) were added thereto at room temperature with stirring, followed by stirring for 30 minutes. After neutralization with a saturated aqueous solution of sodium hydrogencarbonate, the reaction mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/4) to obtain 1,5-bis(methoxymethoxy)-3-{2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]ethyl}-2-bromo-4-ethylbenzene (5.6 g, 93%) as a colorless oil.

Workup

  1. stirringthe reaction mixture was further stirred for 2 hours
  2. extractionextracted twice with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0268732f8d7405686789b84f3ff3af3
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

Loading…