Dimethyl cyclobutane-1,1-dicarboxylate → Methyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

To a solution of 1,1-cyclobutanedicarboxylic acid dimethyl ester (available from Lancaster Synthesis Ltd, UK) (2.0 g, 11.6 mmol) in tetrahydrofuran (20 ml) at room temperature was added lithium tri-tert-butoxyaluminium hydride (25.5 ml of a 1M solution in tetrahydrofuran, 25.5 mmol) dropwise over 10 minutes. The reaction mixture was heated to gentle reflux for 3 hours, cooled to room temperature and stirred for 18 hours. The resulting suspension was diluted with saturated aqueous ammonium chloride (30 ml) and stirred vigorously for 15 minutes before filtering. The solid was washed with diethyl ether (50 ml), the organic layer separated and the aqueous layer extracted with diethyl ether (50 ml). The combined organic extracts were dried over magnesium sulphate, filtered and evaporated in vacuo to give the title compound as a colourless oil (1.8 g).

1. temperatureThe reaction mixture was heated
2. temperatureto gentle reflux for 3 hours
3. stirringstirred vigorously for 15 minutes
4. filtrationbefore filtering
5. washThe solid was washed with diethyl ether (50 ml)
6. customthe organic layer separated
7. extractionthe aqueous layer extracted with diethyl ether (50 ml)
8. dry with materialThe combined organic extracts were dried over magnesium sulphate
9. filtrationfiltered
10. customevaporated in vacuo

ORD record

ord-2ef08f14722d41c18085c414992dcd0f

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07507742B2