Nitromethane → HCID 66693115, compound

HRID 2368012Notes

Reaction equation

HRID 2368012 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([B:14]2[O:18][C:17]([CH3:20])(C)C(C)(C)[O:15]2)=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])C=O)[CH3:2].[N+:23](C)([O-:25])=[O:24]>C1COCC1.[OH-].[Na+]>[CH2:1]([O:3][C:4]1[C:5]2[B:14]([OH:15])[O:18][CH:17]([CH2:20][N+:23]([O-:25])=[O:24])[C:6]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH3:2]

Participants

5

Reactant 2

HCID 6375NitromethaneHCID 86664746HCID 86664746, compound

Product 1

HCID 66693115HCID 66693115, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Synthesized according to the methods of general procedure 9 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: [3-ethoxy-4-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (1.47 g, 4.80 mmol), nitromethane (0.92 g, 14.4 mmol), CATBr (88 mg, 0.24 mmol) in dry THF (20 mL) and NaOH (0.025 M aqueous solution). Purification by silica gel column chromatography (eluant: 10% EtOAc/hexane to 30% EtOAc/hexane) to obtain the title compound as a yellow solid (0.75 g, 59%). 1H NMR {400 MHz, DMSO-d6+D2O (0.01 ml)} δ (ppm) 9.34 (s, 1H), 7.18 (d, J=8.1 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 5.68 (dd, J=9.2, 2.0 Hz, 1H), 5.29 (dd, J=13.2, 2.8 Hz, 1H), 4.55-4.50 (m, 1H), 4.20 (q, J=7.0 Hz, 2H), 3.77 (s, 3H), 1.27 (t, J=7.0 Hz, 3H); MS (ESI) m/z=261 (M−1, negative).

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (eluant: 10% EtOAc/hexane to 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-c865f304f2274e2caaf53c16e14bafc0
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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