4-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate → 3-(2-(4-Bromophenoxy)ethyl)oxetane

HRID 1054875Notes

Reaction equation

HRID 1054875 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]([CH2:24][OH:25])[CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)(=O)=O)=CC=1.C([Li])CCC>O1CCCC1>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH:13]2[CH2:12][O:25][CH2:24]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 866988534-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonateHCID 178418339Butyllithium2×

Product 1

HCID 847090473-(2-(4-Bromophenoxy)ethyl)oxetaneYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate (0.450 g, 1.04 mmol) in anhydrous tetrahydrofuran (10 mL) was added n-butyl lithium (0.42 mL, 2.5 M, 1.04 mmol) dropwise at 0° C. After complete addition of the n-butyl lithium solution, the resulting mixture was heated at reflux overnight. The reaction was carefully quenched with water and extracted with ethyl acetate (5×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by flash chromatography (0-20% ethyl acetate/petroleum ether) to afford the title compound (0.10 g, 37%) as a white solid. 1H NMR (400 MHz, CDCl3) ppm 7.37 (d, 2 H), 6.74 (d, 2 H), 4.89-4.78 (m, 2 H), 4.56-4.45 (m, 2 H), 3.94-3.87 (m, 2 H), 3.30-3.17 (m, 1 H), 2.23-2.12 (m, 2 H)

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThe reaction was carefully quenched with water
  4. extractionextracted with ethyl acetate (5×20 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customThe crude product was purified by flash chromatography (0-20% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5cdc15402e5b4f1f876f5f1a4866918f
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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