9-Anthracenemethanol → HCID 11377511, compound

HRID 2052760Notes

Reaction equation

HRID 2052760 reaction equation
[C:1]([O:8][CH:9]([CH2:11][C:12]1[C:13]2[C:18]([CH:19]=[C:20]3[C:25]=1[CH:24]=[CH:23][CH:22]=[CH:21]3)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].Br[C:27]1[C:28]2[C:33]([CH:34]=[C:35]3[C:40]=1[CH:39]=[CH:38][CH:37]=[CH:36]3)=[CH:32][CH:31]=[CH:30][CH:29]=2.[CH:41]1[C:54]2[C:45](=[CH:46][C:47]3[C:52]([C:53]=2[CH2:55]O)=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:44]=[CH:43][CH:42]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:8][CH:9]([CH2:10][C:27]1[C:40]2[C:35]([CH:34]=[C:33]3[C:28]=1[CH:29]=[CH:30][CH:31]=[CH:32]3)=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:11][C:12]1[C:25]2[C:20]([CH:19]=[C:18]3[C:13]=1[CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:7])[CH2:2][CH2:3][C:4]([O:6][CH2:55][C:53]1[C:54]2[C:45]([CH:46]=[C:47]3[C:52]=1[CH:51]=[CH:50][CH:49]=[CH:48]3)=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:5]

Participants

7

Reactant 4

HCID 738489-AnthracenemethanolHCID 740629-BromoanthraceneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86596292HCID 86596292, compound

Product 1

HCID 11377511HCID 11377511, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1,3-di-(9-anthryl2-propyl hydrogen succinate (4) (103.3 mgr, 0.20 mmoles) prepared from 9-bromoanthracene (A. Castellan, L. Kessab, S. Grelier, A. Nourmamode, M. Cotrait, P. Marsau, J. Chem. Soc. Perkin Trans. 2, 1993, 953-961) (scheme 1), and 9-anthracene methanol (60.7 mgr, 0.29 mmoles), in dry dichloromethane (0.2 ml) a catalytic amount of 4-dimethylaminopyridine (4-DMAP) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (42.48 mgr, 0.222 mmoles) was added, at ice bath temperature. The reaction mixture was stirred overnight under argon, at room temperature and then it was partitioned between water and ethyl acetate. The aqueous phase was washed with ethyl acetate twice and the combined organic extracts were washed with saturated ammonium chloride, water, brine, dried over sodium sulfate and concentrated in vacuo. The crude mixture was subjected to flash chromatography to afford 99.4 mgr (70%) of 1,3-di-(9-anthryl)-2-propyl 9-anthrylmethyl succinate which was further purified by recrystallization from dichloromethane (yellow crystals). 1H NMR (250 MHz, CDCl3): δ 8.35 (5H, m), 8.00 (10H, d), 7.50-7.10 (12H, m), 6.10 (2H, s), 5.70 (1H, m), 4.10 (2H, dd), 3.65 (2H, dd), 2.10 (4H, t); 13C NMR (62.5 MHz, CDCl3): δ 131.54, 131.15, 130.38, 129.62, 128.85, 126.92, 125.38, 124.62, 123.85, 63.85, 31.54, 30.38, 29.23, 28.46 ppm; FTIR 3050.0, 2920.0, 1723.9, 1158.7, 891.3, 731.0 cm−1.

Workup

  1. customit was partitioned between water and ethyl acetate
  2. washThe aqueous phase was washed with ethyl acetate twice
  3. washthe combined organic extracts were washed with saturated ammonium chloride, water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db3606e45e134001ad649c1b060691bf
Source dataset
uspto-grants-2008_02
Patent number
US07326510B2

Reaction notes

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