2',4'-Dihydroxyacetophenone → HCID 69411916, compound

HRID 1868580Notes

Reaction equation

HRID 1868580 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].C(O[C:14](=[O:25])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)C.[CH3:26][C:27]([C:29]1[CH:30]=[CH:31][C:32]([OH:36])=[CH:33][C:34]=1[OH:35])=[O:28]>O1CCCC1>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([C:14](=[O:25])[CH2:26][C:27]([C:29]2[CH:30]=[CH:31][C:32]([OH:36])=[CH:33][C:34]=2[OH:35])=[O:28])[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=1

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 87026Ethyl 3,5-dimethoxybenzoateHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 69411916HCID 69411916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 20% lithiumhexamethyldisilazane in tetrahydrofuran (144 mL, 172 mmol), 2,4-dihydroxy acetophenone, 14 (6.5 g, 43 mmol) in tetrahydrofuran (150 mL) and ethyl-3,5-dimethoxy benzoate, 6 (9 g, 43 mmol) in tetrahydrofuran (100 mL) were reacted to afford 20, 1-(3,5-dimethoxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione (15 g), which was cyclized with Dowex-H+ (5 g) in 2-propanol (200 mL) in a similar way as described for 22 to afford 26. Yield 7.6 g (59%); mp 267-268° C.; MS (FAB) 299 (M++1); IR (KBr) 3405, 1602; 1H NMR (200 MHz, DMSO-d6) δ 10.82 (s, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.17 (d, J=2.0 Hz, 2H), 7.03 (d, J=1.9 Hz, 1H), 6.95 (s, 1H), 6.94 (dd, J=7.2 Hz, 2.0 Hz, 1H), 6.71 (s, 1H), 3.85 (s, 6H).

Sources & evidence

ORD record
ord-6bd9b4bcb55d4ae6bd804e11356ecc2e
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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