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

HRID 855313Notes

Reaction equation

[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Br[C:13]1C=C2C(=C[CH:21]=1)C1(CC1)CC2.[Li]CCCC.CN(C=O)C>>[C:1]12([CH2:2][CH2:3]1)[C:4]1[C:11](=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH2:21][CH2:13]2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 115064744-Cyclopropylbenzaldehyde

HCID 695138995'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]

HCID 178418339Butyllithium

Product 1

HCID 860938352',3'-Dihydrospiro[cyclopropane-1,1'-indene]-5'-carbaldehydeYield 56%

Procedure

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).

Workup

customThe isolated residue was purified by flash column chromatography (1:9 ether:pentane)

Sources & evidence

ORD record: ord-4231f7e8b3fc4266b1cc9cef155da202
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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