Dimethylformamide → 2',3'-Dihydrospiro[cyclopropane-1,1'-indene]-5'-carbaldehyde

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 5′-bromo-2′,3′dihydro-spiro[cyclopropane1,1′-[1H]indene] (345 mg, 1.55 mmol), n-BuLi (1.16 ml, 1.6M solution in hexane, 1.86 mmol) and DMF (481 μl, 6.19 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 2′,3′-dihydro-spiro[cyclopropane-1,1′-[1H]indene]-5′-carboxaldehyde (148 mg, 56%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 9.93 (s, 1H), 7.70 (m, 1H), 7.65 (m, 1H), 6.78 (d, J=8.0 Hz, 1H), 3.10 (apt t, J=8.0 Hz, 2H), 2.18 (apt t, J=8.0 Hz, 2H), 1.08-0.98 (m, 4H).

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