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

HRID 2103058Notes

Reaction equation

HRID 2103058 reaction equation
[C:1]1([C:10](OCC)=[O:11])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3][CH2:2]1>C1COCC1>[OH:11][CH2:10][C:1]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 77410Diethyl 1,1-cyclobutanedicarboxylate

Product 1

HCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl cyclobutane-1,1-dicarboxylate (7.17 mL) was added to a THF (150 mL) suspension of LiAH(OtBu)3 (22.08 g) at room temperature, and the suspension was refluxed for 7 h. The THF was stripped off and the mixture was quenched with water, neutralized with HCl (3 M) and extracted with dichloromethane and ethylacetate. The combined organic phases were washed with brine, dried and evaporated. The crude residue was put on a column and eluted with DCM : EtOAc; 5:1 to give ethyl 1-(hydroxymethyl)-cyclobutanecarboxylate (4.08 g) as a clear oil. 1H-NMR (300 MHz, CDCl3), δ=4.3372-4.1188 (q, 2H); 3.9337-3.7479 (d, 2H); 2.5485-2.322 (m, 3H); 2.1117-1.9015 (m, 4H); 1.3963-1.2174 (t, 3H) ppm.

Workup

  1. temperaturethe suspension was refluxed for 7 h
  2. customthe mixture was quenched with water
  3. extractionextracted with dichloromethane and ethylacetate
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. customevaporated
  7. washeluted with DCM

Sources & evidence

ORD record
ord-c947ea89a4f441788bf97e3b2a151128
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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