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

HRID 352989

Reaction equation

HRID 352989 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c5ae8adf6990431d9f515109f7052bd9
Source dataset
uspto-grants-2004_06
Patent number
US06749756B1

Linked notes

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