Benzyl Bromide → Butyl 3-(benzyloxy)cyclobutane-1-sulfonate

HRID 1259428Notes

Reaction equation

HRID 1259428 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:7][CH:6]([S:8]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:10])=[O:9])[CH2:5]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>C1COCC1.CCCCCC>[CH2:16]([O:3][CH:4]1[CH2:7][CH:6]([S:8]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:10])=[O:9])[CH2:5]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86656333Butyl 3-hydroxycyclobutane-1-sulfonate

Product 1

HCID 58380564Butyl 3-(benzyloxy)cyclobutane-1-sulfonateYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

60% NaH (0.95 g, 2.52 (CH2)2CH3 mmol) was added to a cooled solution of butyl 3-hydroxycyclobutane-1-sulfonate (0.35 g, 1.68 mmol) in dry THF (20 mL) at 0° C. and the resulting reaction mass was stirred at room temperature for 30 minutes. This was followed by the addition of benzyl bromide (0.43 g, 2.52 mmol) and stirred the resulting mixture at room temperature for 2 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was quenched with ice-water and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (4% ethyl acetate in hexane) afforded 0.2 g of the product (50% yield).

Workup

  1. customthe resulting reaction mass
  2. stirringstirred the resulting mixture at room temperature for 2 hours
  3. customThe reaction mixture was quenched with ice-water
  4. extractionextracted
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel (4% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b8fd769172694eb887407d4e4e279917
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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