Ethyl Acetate → 5-[4-(2-Azepan-1-yl-ethoxy)-phenyl]-5-methyl-5,11-dihydro-chromeno[4,3-c]chromene-2,8-diol

HRID 2055041Notes

Reaction equation

HRID 2055041 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[C:24]([C:26]4[CH:41]=[CH:40][C:29]([O:30][CH2:31][CH2:32][N:33]5[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)([CH3:25])[O:23][C:22]4[CH:21]=[C:20]([O:42][Si](C(C)(C)C)(C)C)[CH:19]=[CH:18][C:17]=4[C:12]=3[CH2:13][O:14][C:15]=2[CH:16]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-].C(OCC)(=O)C>C1COCC1>[N:33]1([CH2:32][CH2:31][O:30][C:29]2[CH:28]=[CH:27][C:26]([C:24]3([CH3:25])[C:11]4[C:10]5[CH:9]=[CH:8][C:7]([OH:6])=[CH:16][C:15]=5[O:14][CH2:13][C:12]=4[C:17]4[CH:18]=[CH:19][C:20]([OH:42])=[CH:21][C:22]=4[O:23]3)=[CH:41][CH:40]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 219592481-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane

Product 1

HCID 219592555-[4-(2-Azepan-1-yl-ethoxy)-phenyl]-5-methyl-5,11-dihydro-chromeno[4,3-c]chromene-2,8-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane (77.5 mg, 0.11 mmol) in THF (7 mL) was added tetrabutylammonium fluoride (1M in THF, 213 μL, 0.21 mmol). The mixture was stirred at room temperature for 40 min. Saturated NH4Cl was then added followed by addition of ethyl acetate. The resulting layers were separated, organic layer was washed with brine, and dried over MgSO4. The remaining solvent was evaporated and the residue dried under vacuum for 2 h at room temperature to yield the title compound, which was carried on to the next step without further purification.

Workup

  1. customThe resulting layers were separated
  2. washorganic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe remaining solvent was evaporated
  5. customthe residue dried under vacuum for 2 h at room temperature

Sources & evidence

ORD record
ord-10804fa0a3394438839a3a63f5feafb6
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

Loading…