Synthesis of 2-(3’,3’-dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol

Synthesis of 2-(3’,3’-dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol

Preparation of 2-(3’,3’-dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol

Preparation of 2-(3’,3’-dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol

Preparation of 2-(3’,3’-dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol

Synthesis of spiropyran laurate (SPL) derivative: 2-(3’,3’-Dimethyl-6-nitro-3’H-spiro[chromen-2,2’-indol]-1’-yl)-ethanol 1 (0.50 g, 1.42 mmol) was dissolved in dry dichloromethane (10 mL) together with triethylamine (0.39 mL, 2.84 mmol), under nitrogen. Lauroyl chloride (0.33 mL, 1.42 mmol) was then added via syringe at room temperature. After stirring for 10 min the reaction mixture was passed through a plug of silica gel, the solvent evaporated in vacuo and the residue purified by column chromatography (SiO2, EtOAc/hexanes, 1:3). 1H NMR (400 MHz, d6-acetone)  8.15 (d, J = 2.8 Hz, 1H), 8.05 (dd, J = 8.9, 2.8 Hz, 1H), 7.21 (d, J = 10.4 Hz, 1H), 7.19-7.13 (m, 2H), 6.85 (m, 2H), 6.76 (d, J = 7.8 Hz, 1H), 6.09 (d, J = 10.4 Hz, 1H), 4.25 (m, 2H), 3.56 (m, 1H), 3.46 (m, 1H), 2.24 (td, J = 7.5, 2.1 Hz, 2H), 1.53 (m br, 2H), 1.27 (m, 21H), 1.18 (s, 3H), 0.88 (t br, 3H) ppm.

Supporting Information “Alkylation of Spiropyran Moiety Provides Reversible Photo-control over Nanostructured Soft Materials”, by Wye-Khay Fong et al.  Original article: Wye-Khay Fonget al., Biointerphases 7, 3 (2012); http://dx.doi.org/10.1007/s13758-011-0003-9

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