2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 87737248, compound

HRID 2252504Notes

Reaction equation

HRID 2252504 reaction equation
[CH3:1][O:2][C:3](=[O:76])/[CH:4]=[CH:5]\[CH:6]=[CH:7]\[C@@H:8]([CH3:75])[C@@H:9]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:10][C@H:11]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])/[CH:12]=[CH:13]\[C@H:14]([CH3:58])[C@H:15]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[C@@H:16]([CH3:49])[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[C@H:22]([CH3:40])[C@@H:23]([O:30]CC1C=CC(OC)=CC=1)[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:3](=[O:76])/[CH:4]=[CH:5]\[CH:6]=[CH:7]\[C@@H:8]([CH3:75])[C@@H:9]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:69])[CH3:70])[CH2:10][C@H:11]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:61])[CH3:62])/[CH:12]=[CH:13]\[C@H:14]([CH3:58])[C@H:15]([O:50][Si:51]([C:54]([CH3:55])([CH3:56])[CH3:57])([CH3:53])[CH3:52])[C@@H:16]([CH3:49])[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([O:41][Si:42]([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:43])[CH3:44])[C@H:22]([CH3:40])[C@@H:23]([OH:30])[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 87735827HCID 87735827, compound

Product 1

HCID 87737248HCID 87737248, compoundYield 81,714.703%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The procedure for 47 was used with 76 (0.38 g, 0.34 μmol) and DDQ (0.084 g, 0.37 mmol) to yield 77 (0.28 g, 82%) after flash column chromatography (EtOAc/hexane 1:9) as a colorless oil: IR (CHCl3) 3542, 2956, 2856, 1722, 1640, 1462, 1254, 1175, 1086, 1004, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.39 (dd, J=15.2, 11.2 Hz, 1H), 6.63 (ddd, J=16.9, 10.5, 10.4 Hz, 1H), 6.53 (t, J=11.3 Hz, 1H), 6.09 (t, J=1.0 Hz, 1H), 5.98 (dd, J=8.3, 7.1 Hz, 1H), 5.58 (d, J=11.3 Hz, 1H), 5.45-5.39 (m, 2H), 5.26 (dd, J=10.8, 8.4 Hz, 1H), 5.20 (d, J=16.9 Hz, 1H), 5.11(d, J=10.1 Hz, 1H), 4.53 (m, 1H), 3.95 (m, 1H), 3.76 (m, 1H), 3.71 (s, 3H), 3.47 (m, 1H), 3.40 (m, 1H), 2.82 (m, 1H), 2.55 (m, 1H), 2.20 (br, 1H), 1.72 (m, 2H), 1.60-1.35 (m, 5H), 1.32-1.10 (m, 5H), 1.04 (d, J=6.8 Hz, 3H), 0.99-0.83 (m, 48H), 0.12-0.03 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 166.7, 147.1, 145.4, 135.2, 132.6, 132.5, 132.3, 130.0, 126.8, 117.7, 115.5, 80.2, 77.3, 76.2, 72.1, 66.5, 50.9, 43.4, 42.5, 38.3, 38.1, 36.1, 35.8, 34.7, 33.7, 28.3, 26.2, 25.94, 25.89, 25.5, 19.5, 18.4, 18.1, 17.7, 14.9, 13.3, 7.2, −3.0, −3.6, −3.8, −4.18, −4.20, −4.37, −4.41; LRMS (ESI) 1029.7 [M+Na]+, 875.6, 379.3; HRMS (ESI) calcd for C56H110O7Si4Na 1029.7226 [M+Na]+, found 1029.7244; [α]20D−18.7 (c 0.62, CHCl3).

Sources & evidence

ORD record
ord-9761a336ac6643e0819769a5bb612923
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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