Ethyl Acetate → 3-(Benzyloxy)cyclobutane-1-sulfonyl chloride

HRID 1259430Notes

Reaction equation

HRID 1259430 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH2:6]([O:13][CH:14]1[CH2:17][CH:16]([S:18]([O-:21])(=O)=[O:19])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[K+].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[CH2:6]([O:13][CH:14]1[CH2:17][CH:16]([S:18]([Cl:3])(=[O:21])=[O:19])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 86656336Potassium 3-(benzyloxy)cyclobutane-1-sulfonate

Product 1

HCID 583805353-(Benzyloxy)cyclobutane-1-sulfonyl chlorideYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

POCl3 (0.34 mL, 3.558 mmol) was added to a cooled solution of potassium 3-(benzyloxy)cyclobutane-1-sulfonate (0.5 g, 1.779 mmol) in dry DCM (10 mL) at 0° C. This was followed by the slow addition of diisopropyl ethyl amine (0.65 mL, 3.558 mmol) and stirred the resulting reaction mixture at 0° C. for 2 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was extracted with DCM. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 0.15 g of the product (38% yield).

Workup

  1. customthe resulting reaction mixture at 0° C. for 2 hours
  2. extractionThe reaction mixture was extracted with DCM
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-960729471ea94814b5bfa01cf023c0ef
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…