Diethyl 1,1-cyclobutanedicarboxylate → Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

HRID 1809427Notes

Reaction equation

HRID 1809427 reaction equation
[Li+].CC(O[Al-](OC(C)(C)C)OC(C)(C)C)(C)C.[C:18]1([C:27](OCC)=[O:28])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19]1.OS([O-])(=O)=O.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:25]([O:24][C:22]([C:18]1([CH2:27][OH:28])[CH2:21][CH2:20][CH2:19]1)=[O:23])[CH3:26]

Participants

6

Reactant 3

HCID 77410Diethyl 1,1-cyclobutanedicarboxylateHCID 516920Potassium bisulfateHCID 16688073Lithium aluminum-tri-tert-butoxyhydride

Product 1

HCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylateYield 63.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of lithium aluminum-tri-tert-butoxyhydride 1.0M in THF (100.0 mL, 100.0 mmol) is added at −78° C. to a solution of diethyl 1,1-cyclobutanedicarboxylate (10.0 g, 50.0 mmol) in anhydrous THF (50.0 mL). After stirring the reaction mixture at room temperature for 14 h, 10% aq. KHSO4 solution is added and the reaction mixture diluted with ethyl acetate. After separating the two phases, the organic phase is washed with water and brine and dried over anhydrous Na2SO4. Filtration and removal of the solvent under reduced pressure affords 5.0 g of 1-hydroxymethyl-cyclobutanecarboxylic acid ethyl ester that is used in the next step without further purification. Yield: 63%; m/z 159 [M+H].

Workup

  1. customAfter separating the two phases
  2. washthe organic phase is washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6a87c1386f08414da8609056a9cbbd11
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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