Triethylamine → 1-[3-(tert-Butyldimethylsilanyl)-prop-2-ynyl]-4-[1-(dimethyloctylsilanyloxy)-2-phenylethyl]-6-iodo-3-methyl-1H-pyridin-2-one

HRID 352989

Reaktionsgleichung

Reaktionsgleichung von HRID 352989
[Si:1]([C:8]#[C:9][CH2:10][N:11]1[C:16]([I:17])=[CH:15][C:14]([CH:18]([OH:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]([CH3:27])[C:12]1=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.Cl[Si:37]([CH3:47])([CH3:46])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:1]([C:8]#[C:9][CH2:10][N:11]1[C:16]([I:17])=[CH:15][C:14]([CH:18]([O:26][Si:37]([CH3:46])([CH3:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:13]([CH3:27])[C:12]1=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 87482ChlorodimethyloctylsilaneHCID 227066981-[3-(tert-butyldimethylsilanyl)prop-2-ynyl]-4-(1-hydroxy-2-phenylethyl)-6-iodo-3-methyl-1H-pyridin-2-one

Produkt 1

HCID 102119661-[3-(tert-Butyldimethylsilanyl)-prop-2-ynyl]-4-[1-(dimethyloctylsilanyloxy)-2-phenylethyl]-6-iodo-3-methyl-1H-pyridin-2-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[3-(tert -butyldimethylsilanyl)prop-2-ynyl]-4-(1-hydroxy-2-phenylethyl)-6-iodo-3-methyl-1H-pyridin-2-one 4a (60 mg, 0.12 mmol) and 4-dimethylaminopyridine (2 mg, 1.2 μmol) in CH2Cl2 (2 mL) was added NEt3 (49 mg, 66 μL, 0.48 mmol) and chlorodimethyloctylsilane (62 mg, 77 μL, 0.3 mmol). The resulting mixture was stirred for 12 h. The solvent was evaporated and the residue was purified by flash chromatography (hexanes-EtOAc 15:1) to afford 5a (41 mg, 51%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ7.32-7.24 (m, 3H), 7.15-7.12 (m, 2H), 7.08 (s, 1H), 5.14 (d, J=17.0, 1H), 5.09 (d, J=17.0, 1H), 4.79 (t, J=6.4 Hz, 1H), 2.79 (d, J=6.4 Hz, 2H), 1.98 (s, 3H), 1.39-1.11 (m, 14H), 0.94 (s, 9H), 0.90-0.87 (m, 3H), 0.10 (s, 6H), −0.17 (s, 3H), −0.18 (s, 3H); 13C NMR (75 MHz, CDCl3) δ162.3, 152.0, 137.8, 129.7, 129.1, 128.3, 127.5, 127.2, 126.6, 118.6, 88.4, 44.6, 33.5, 32.0, 29.4, 29.3, 26.1, 23.2, 23.0, 22.7, 17.9, 16.5, 14.2, 12.0, −0.19, −2.05, −4.78.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (hexanes-EtOAc 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-c5ae8adf6990431d9f515109f7052bd9
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06749756B1

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