tert-BUTYL CHLORIDE → HCID 59172000, Verbindung

HRID 1952424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952424
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:30]([CH3:33])([CH3:32])[CH3:31]>>[C:30]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH2:14][CH2:15][CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][C:3]([C:5]([CH3:6])([CH3:13])[CH3:4])=[CH:2][CH:1]=3)([CH3:33])([CH3:32])[CH3:31]

Komponenten

4

Edukt 3

HCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) Chloride2×HCID 59172007HCID 59172007, Verbindung

Produkt 1

HCID 59172000HCID 59172000, Verbindung

Versuchsvorschrift

Diethyl 3-(9H-carbazol-9-yl)propylphosphonate (1.00 g, 2.89 mmol) was dissolved in 2-chloro-2-methylpropane (5.0 mL) and flushed with N2 for 5 minutes. To this stirred solution was added aluminum chloride (1.16 g, 8.67 mmol) slowly. The solution turned chunky and black with gas bubbles appearing. The reaction was allowed to stir for 25 minutes after adding all the aluminum chloride. It was then quenched with 25 mL water and an extraction performed with water washings followed by 2×20 mL 1 M NaOH washings, then another water washing. The yellow organic layer was kept and dried and the solvent removed under vacuum. A tlc in ethyl acetate showed 4 spots with the brightest (and desired product) being the third spot from the top. A long column was run and the desired product was obtained as a thick yellow oil (447 mg, 34% yield). 1H NMR (400.14 MHz, CD2Cl2) δ 8.10 (d, J=1.6 Hz, 2H), 7.52 (dd, J=8.80, 2.00 Hz, 2H), 7.35 (d, 8.40 Hz, 2H), 4.36 (t, J=7.00 Hz, 2H), 4.08-3.93 (m, 4H), 2.21-2.07 (m, 2H), 1.71 (dt, J=18.14 Hz, 6.00 Hz, 2H), 1.45 (18H), 1.25 (t, J=7.00 Hz, 6H). 13C{1H} NMR (100.61 MHz, CD2Cl2) δ 142.14 (2C), 139.26 (2C), 123.80 (2C), 123.06 (2C), 116.68 (2C), 108.50 (2C), 61.89 (d, J=6.4 Hz, 2C), 43.36 (d, J=15.8 Hz), 34.92 (2C), 32.19 (6C), 23.35 (d, 142.2 Hz), 22.59 (d, J=4.9 Hz), 16.64 (d, J=5.8 Hz, 2C). 31P{1H} NMR (161.97 MHz, CD2Cl2): δ 31.34.

Aufarbeitung

  1. customflushed with N2 for 5 minutes
  2. customIt was then quenched with 25 mL water
  3. extractionan extraction
  4. customdried
  5. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-145a6433800e4737b980314d46dda342
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08405069B2

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