Trifluoroacetic acid → HCID 68898935, compound

HRID 1435927Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([N+:21]([O-:23])=[O:22])=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].COC1C([N+]([O-])=O)=C(C=CC=1)C=O.CO[CH2:39][N:40]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:41][Si](C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:46]([N:40]1[CH2:41][CH:6]([C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([O:2][CH3:1])[C:4]=2[N+:21]([O-:23])=[O:22])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:39]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of diethyl 2-(3-methoxy-2-nitrobenzylidene)malonate, which was prepared from 3-methoxy-2-nitrobenzaldehyde following the procedure described in Example 1, Part C (162 mg, 0.5 mmol) in 10 mL of methylene chloride was added added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (237 mg, 1.0 mmol) and trifluoroacetic acid (0.010 mL, 0.125 mmol). The solution was allowed to stir at 40° C. for 18 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (elution with 4:1 hexane/EtOAc) to afford 201 mg (88%) of the title compound. 1H NMR (CDCl3): δ 7.40-7.25 (m, 7H), 6.93-6.85 (m, 1H), 4.36-4.30 (m, 1H), 4.32-4.15 (m, 2H), 3.87 (s, 3H), 3.77 (q, 2H), 3.69 (s, 2H), 3.60-3.50 (m, 1H), 3.05-2.97 (m, 1H), 2.85-2.78 (m, 1H), 2.75-2.68 (m, 1H), 1.23 (t, 3H, J=7.2 Hz), 0.83 (t, 3H, J=7.2 Hz). LRMS (ESI): 457.4 (M+H)+.

Workup

additionwas added
concentrationThe reaction mixture was concentrated in vacuo
custompurified by flash chromatography (elution with 4:1 hexane/EtOAc)

Sources & evidence

ORD record: ord-b08bf9715a1e4ed4b4f6537b171134aa
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618980B2

Reaction notes

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