Ethyl Acetate → Butyl 3-(1,3-dihydroxypropan-2-yl)cyclobutane-1-sulfonate

HRID 1259403Notes

Reaction equation

HRID 1259403 reaction equation
B.CSC.[CH2:5]([O:9][S:10]([CH:13]1[CH2:16][C:15](=[C:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH2:14]1)(=[O:12])=[O:11])[CH2:6][CH2:7][CH3:8].C(OCC)(=O)C>C1COCC1>[OH:19][CH2:18][CH:17]([CH:15]1[CH2:14][CH:13]([S:10]([O:9][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:12])=[O:11])[CH2:16]1)[CH2:23][OH:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58380583Diethyl 2-(3-(butoxysulfonyl)cyclobutylidene)malonate

Product 1

HCID 58380541Butyl 3-(1,3-dihydroxypropan-2-yl)cyclobutane-1-sulfonateYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-DMS (0.2 mL, 2.3 mmol) was added to a solution of diethyl 2-(3-(butoxysulfonyl)cyclobutylidene)malonate (0.2 g, 0.575 mmol) in THF (5 mL) and the resulting reaction mass was stirred at room temperature overnight. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was quenched with 1N HCl and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. Purification by column chromatography on silica gel (70% ethyl acetate in hexane) afforded 0.13 g of the product (74% yield).

Workup

  1. customthe resulting reaction mass
  2. customThe reaction mixture was quenched with 1N HCl
  3. extractionextracted
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0d57d6b9d56a41c48d7a42e7a85a3f92
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…