Water → HCID 118308794, compound

HRID 1481992Notes

Reaction equation

HRID 1481992 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13]Cl)[CH2:2][CH:3]=[CH2:4].[C:15]1([C:21](=[N:28][CH2:29][C:30]#[N:31])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][CH:29]([N:28]=[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:30]#[N:31])[CH2:2][CH:3]=[CH2:4]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 118308888HCID 118308888, compound

Product 1

HCID 118308794HCID 118308794, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(but-3-en-1-yloxy)-2-(chloromethyl)-4-fluorobenzene (1 g, 4.66 mmol, 1 equiv), 2-((diphenylmethylene)amino)acetonitrile (1.13 g, 5.12 mmol, 1.1 equiv), and benzyltrimethylammonium chloride (87 mg, 0.466 mmol, 0.1 equiv) in DCM (8 mL) was added 10 N NaOH (0.84 mL, 8.39 mmol, 1.8 equiv). After 44 h, add to water and extract with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-30% EtOAc/hexane) to provide the product (1.39 g, 75%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.62-7.54 (m, 2H), 7.49-7.33 (m, 5H), 6.96-6.74 (m, 5H), 6.61 (dd, J=8.8, 4.3 Hz, 1H), 5.58 (ddt, J=17.1, 10.2, 6.8 Hz, 1H), 5.18-4.97 (m, 2H), 4.65 (dd, J=9.2, 4.6 Hz, 1H), 3.81 (dt, J=8.7, 6.3 Hz, 1H), 3.62-3.45 (m, 1H), 3.37 (dd, J=13.1, 4.8 Hz, 1H), 3.15 (dd, J=13.1, 9.3 Hz, 1H), 2.24 (q, J=6.6 Hz, 2H).

Workup

  1. extractionextract with DCM (×3)
  2. dry with materialThe combined DCM extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-bdd1132e8a7240bf8adb487a192d542d
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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