Trifluoroacetic acid → HCID 11998203, compound

HRID 545948Notes

Reaction equation

[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:25]3[C:17](=[CH:18][C:19]4[O:20][CH2:21][O:22][C:23]=4[CH:24]=3)[C:16](=O)[CH2:15]2)[C:7]1=[O:27])[CH2:2][CH2:3][CH2:4][CH3:5].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:25]3[C:17](=[CH:18][C:19]4[O:20][CH2:21][O:22][C:23]=4[CH:24]=3)[CH2:16][CH2:15]2)[C:7]1=[O:27])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 11998204HCID 11998204, compound

Product 1

HCID 11998203HCID 11998203, compoundYield 52%

Procedure

A mixture of 1′-pentylspiro[indeno[5,6-d][1,3]dioxole-5,3′-indole]-2′,7(1′H,6H)-dione (0.04 g, 0.11 mmol), triethylsilane (1.50 mL) and trifluroacetic acid (2.00 mL, excess) was stirred at ambient temperature overnight. The mixture was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.02 g, 47%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.25 (td, 1H), 7.06-6.95 (m, 2H), 6.88 (d, 1H), 6.77 (s, 1H), 6.05 (s, 1H), 5.88-5.82 (m, 2H), 3.81-3.60 (m, 2H), 3.37-3.24 (m, 1H), 3.13-3.01 (m, 1H), 2.70-2.59 (m, 1H), 2.44-2.32 (m, 1H), 1.76-1.64 (m, 2H), 1.39-1.28 (m, 4H), 0.88 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 179.5, 147.9, 147.0, 142.9, 138.2, 136.7, 134.7, 128.1, 123.5, 122.6, 108.3, 105.3, 103.6, 101.2, 59.9, 40.0, 38.3, 31.6, 29.0, 27.1, 22.6, 14.0; MS (ES+) m/z 372.1 (M+23), 350.1 (M+1).

Workup

concentrationThe mixture was concentrated in vacuo to dryness

Sources & evidence

ORD record: ord-cd4a7043f2ac46e3b6a02b19c1d3b4a4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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