Methyl 3,3-dimethoxycyclobutane-1-carboxylate → (3,3-Dimethoxycyclobutyl)methanol

HRID 1241501Notes

Reaction equation

HRID 1241501 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][C:7]([O:11][CH3:12])([O:9][CH3:10])[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:10][O:9][C:7]1([O:11][CH3:12])[CH2:8][CH:5]([CH2:3][OH:2])[CH2:6]1

Participants

4

Reactant 2

HCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10486988(3,3-Dimethoxycyclobutyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester, (J. Org. Chem. 1988, 53, 3841 and J. Org. Chem. 1996, 61, 2174) (15.0 g, 86.1 mmol) in 40 mL of tetrahydrofuran at 0° C. (ice/water bath) was added dropwise a solution of lithium aluminum hydride (103.3 mL, 1M tetrahydrofuran). After the addition was complete the reaction was warmed to room temperature and stirred 12 hours. The reaction was worked-up using the method of Feiser and Feiser, and then filtered through a plug of Celite and concentrated under reduced pressure to yield (3,3-dimethoxy-cyclobutyl)-methanol (12.4 g, 99% crude yield) as a colorless oil. This material was used without further purification.

Workup

  1. additionAfter the addition
  2. filtrationfiltered through a plug of Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bafaa5cc77314afaa5aac3cc04480399
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

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