Potassium Carbonate → HCID 16086954, compound

HRID 1724118Notes

Reaction equation

HRID 1724118 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)=[CH:7][CH:6]=1)=[O:4].[CH2:31]([O:41][C:42]1[CH:43]=[C:44]([OH:59])[CH:45]=[C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:47]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].C([O-])([O-])=O.[K+].[K+]>C1(=O)CCCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:59][C:44]2[CH:45]=[C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:47]=[C:42]([O:41][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:43]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16086950HCID 16086950, compoundHCID 57560093HCID 57560093, compound

Product 1

HCID 16086954HCID 16086954, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A mixture of compound 19b (540 mg, 1.13 mmol), phenol 9 (461 mg, 1.13 mmol), K2CO3 (392 mg, 2.83 mmol), and a catalytic amount of KI in cyclohexanone (6.50 ml) is reacted in analogy to the already described reaction instructions for the synthesis of compound 20a. The subsequent purification through column chromatography (silica gel, ethyl acetate/petroleum ether 1:2) produced 768 mg (85%) of compound 20b as colorless oil. IR (film) 2900, 2830, 1710, 1650, 1590 cm−1; 1H-NMR (CDCl3) δ 8.00 (d, 8.6 Hz, 2H), 7.94 (d, 8.4 Hz, 2H), 7.25 (d, 8.4 Hz, 2H), 7.05 (d, 8.6 Hz, 2H), 6.05 (t, 1.9 Hz, 1H), 6.02 (d, 1.9 Hz, 2H), 4.95 (s, 2H), 3.92 (s, 3H), 3.91-3.82 superimposed signals (3.90, s, 3H and m, 6H), 2.12 (t, 7.4 Hz, 2H), 1.80-1.61 (m, 8H), 1.47-1.20 (m, 30H), 0.88 (t, 6.7 Hz, 6H); MS (FD) m/z 802 (M+). Anal. calc. for C49H71NO8: C, 73.37; H, 8.92; N, 1.75. Found C, 73.25; H, 8.78; N, 1.87.

Workup

  1. customThe subsequent purification through column chromatography (silica gel, ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-6df67549e8e247d7a6965f32250836c5
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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