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

HRID 2214296Notes

Reaction equation

HRID 2214296 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:39]=[CH:38][C:29]([O:30][CH2:31][CH2:32][N:33]5[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:40][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>[CH3:25][C:24]1([C:26]2[CH:39]=[CH:38][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([OH:6])=[CH:16][C:15]=3[O:14][CH2:13][C:12]=2[C:17]2[CH:18]=[CH:19][C:20]([OH:40])=[CH:21][C:22]=2[O:23]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 219592841-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-pyrrolidine

Product 1

HCID 219591455-Methyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-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)-pyrrolidine (84.5 mg, 0.12 mmol) in THF (7 mL) was added tetrabutylammonium fluoride (1M in THF, 241.4 μL, 0.24 mmol). The mixture was stirred at room temperature for 40 min. Saturated NH4Cl was added followed by addition of ethyl acetate. The resulting layers were separated, the organic layer was washed with brine, and dried over MgSO4. The 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. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customthe residue dried under vacuum for 2 h at room temperature

Sources & evidence

ORD record
ord-59ebf7e8cfb041c08b4f3e0e357c4140
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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