HCID 68946822, compound → HCID 57766449, compound

HRID 1967700Notes

Reaction equation

HRID 1967700 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH2:12][CH:13]([OH:23])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:10][CH:11]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH2:12][C:13](=[O:23])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 68946822HCID 68946822, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 57766449HCID 57766449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-tert-butyl 3-(3-(2,6-dichlorostyryl)phenyl)-2-hydroxypropylcarbamate (1.08 g, 2.56 mmol) in CH2Cl2 (20 mL) was added Celite (0.8 g) and pyridinium chlorochromate (0.661 g, 3.06 mmol). The reaction mixture was stirred at room temperature for 1.5 h then additional Celite (0.70 g) and pyridinium chlorochromate (0.552 g, 2.56 mmol) were added. The mixture was stirred for 1 h then the solids were removed by filtration through Celite. The filtrate was concentrated under reduced pressure then purified by flash chromatography (10 to 70% EtOAc-hexanes gradient) to give (E)-tert-butyl 3-(3-(2,6-dichlorostyryl)phenyl)-2-oxopropylcarbamate. Yield (0.49 g, 45%): 1H NMR (400 MHz, DMSO-d6) δ 7.52 (d, J=8.4 Hz, 2H), 7.48 (d, J=7.8 Hz, 1H), 7.42 (s, 1H), 7.29-7.36 (m, 2H), 7.15 (d, J=7.4 Hz, 1H), 7.12 (d, J=16.6 Hz, 1H), 7.04 (d, J=16.6 Hz, 1H), 7.05-7.06 (m, 1H), 3.88 (d, J=6.0 Hz, 2H), 3.78 (s, 2H), 1.36 (s, 9H).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customthe solids were removed by filtration through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthen purified by flash chromatography (10 to 70% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-ff3de8b880304e0d8abadd164f8ae3a1
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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