Ethyl Acetate → (3,3-Dimethoxycyclobutyl)methanol

HRID 546173Notes

Reaction equation

HRID 546173 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-].C(OCC)(=O)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:10][O:9][C:7]1([O:11][CH3:12])[CH2:8][CH:5]([CH2:3][OH:2])[CH2:6]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62649Sodium sulfate decahydrateHCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10486988(3,3-Dimethoxycyclobutyl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester (1.48 g, 8.49 mmol) in tetrahydrofuran (5 ml) was added dropwise to a cooled 0° C. suspension of lithium aluminum hydride (0.39 g, 10.19 mmol) in tetrahydrofuran (15 ml). The reaction was allowed to warm to 25° C. and stirred for 17 h. After such time, ethyl acetate (1 ml) and a few crystals of sodium sulphate decahydrate were added with caution and stirred until gas evolution stopped. The resulting residue was filtered through a short celite pad and washed with ethyl acetate and then concentrated in vacuo to afford (3,3-dimethoxy-cyclobutyl)-methanol (1.04 g, 84%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.57 (brs, 1H, OH), 1.82-1.97 (m, 2H, CH2), 2.23-2.36 (m, 3H, CH2 and CH), 3.14 (s, 3H, OCH3), 3.16 (s, 3H, OCH3), 3.64-3.68 (m, 2H, OCH2).

Workup

  1. stirringstirred until gas evolution
  2. filtrationThe resulting residue was filtered through a short celite pad
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96c632b718324ce48c10fb38aad4b33e
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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