Nitromethane → HCID 66693063, compound

HRID 2368003Notes

Reaction equation

HRID 2368003 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([B:23]2[O:27][C:26](C)(C)[C:25](C)(C)[O:24]2)=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:32](C)([O-:34])=[O:33].[OH-].[Na+].C1COCC1>O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]2[B:23]([OH:27])[O:24][CH:25]([CH2:26][N+:32]([O-:34])=[O:33])[C:15]=2[CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 87111485HCID 87111485, compound

Product 1

HCID 66693063HCID 66693063, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesized according to the methods of general procedure 8 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: 3-(3-benzyloxy-propoxy)-4-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (3.36 g, 7.88 mmol), nitromethane (1.28 mL, 23.66 mmol), NaOH (0.22 g, 5.52 mmol), THF (6 mL), water (18 mL). Purification: flash column chromatography (30% EtOAc/hexanes): yield 1.2 g (41%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.36 (s, 1H), 7.40-7.22 (m, 5H), 7.22-7.04 (m, 2H), 5.68 (dd, J=9.4, 2.7 Hz, 1H), 5.29 (dd, J=13.4, 2.5 Hz, 1H), 4.52 (dd, J=13.3, 9.4 Hz, 1H), 4.45 (s, 2H), 4.25 (t, J=6.2 Hz, 2H), 3.75 (s, 3H), 3.61 (t, J=6.2 Hz, 2H), 1.92 (quin, J=6.5 Hz, 2H).

Workup

  1. customSynthesized
  2. customPurification

Sources & evidence

ORD record
ord-54c79e05653543c39665bdee517a08ef
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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