4-Nitrophenol → 2-(14-(4-Nitrophenoxy)-3,6,9,12-tetraoxatetradecyloxy)tetrahydro-2H-pyran

HRID 78710Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[N+:39]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)([O-:41])=[O:40]>CN(C=O)C.O>[N+:39]([C:42]1[CH:47]=[CH:46][C:45]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:44][CH:43]=1)([O-:41])=[O:40]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 27 (2.90 g, 6.09 mmol) in anhydrous DMF (11 mL) were added K2CO3 (2.53 g, 18.3 mmol) and 4-nitrophenol (0.847 g, 6.09 mmol), and the reaction mixture was heated to 80° C. for 16 h. After cooling, the reaction mixture was diluted in water, extracted three times with CH2Cl2, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give 28 as an oily residue (2.65 g, 98%): 1H NMR (300 MHz, CDCl3) δ 8.18 (d, J=9.2 Hz, 2H), 6.99 (d, J=9.2 Hz, 2H), 4.69-4.56 (m, 1H), 4.28-4.17 (m, 2H), 3.97-3.42 (m, 18H), 1.95-1.41 (m, 6H). 13C NMR (75 MHz, CDCl3) δ 163.82, 141.40, 125.75, 114.52, 98.83, 70.81, 70.51, 70.43, 69.27, 68.15, 66.54, 62.12, 30.48, 25.34, 19.41.

Workup

temperatureAfter cooling
extractionextracted three times with CH2Cl2
dry with materialdried over MgSO4
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-187986b35c214013bf8b9e9acf5416d4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841460B2

Reaction notes

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