Potassium Carbonate → Dibenzyl ether

HRID 1675909

Reaction equation

HRID 1675909 reaction equation
[CH3:1][C@@:2]12C(=O)CC[C@H:15]1[C@H:14]1[C@@H:5](C3C(CC1)=CC(O)=C(OC)C=3)[CH2:4][CH2:3]2.[C:23]([O-:26])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:26][CH2:23][C:2]1[CH:15]=[CH:14][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 4406242-Methoxyestrone

Product 1

HCID 7657Dibenzyl etherYield 379.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 2-Methoxy estrone (0.521 g, 0.00173 mol) was dissolved in anhydrous DMF under nitrogen atmosphere, added K2CO3 (0.718 g, 0.00225 mol) and stirred at r.t. for approximately 40 h. The crude mixture was diluted with EtOAc, washed with water and brine. The organics were dried (MgSO4) and concentrated. The crude product was pre-absorbed onto silica gel, purified using Flash Master-2 system to give the benzylated compound 32 (0.651 g, 96%) as a chalky white solid: TLC (Rt, 0.4, EtOAc:Hexane, 3:7); 1H NMR (270 MHz, CDCl3) δ 0.90 (s, 3H, 18-CH3 diastereomeric methyl signals), 1.24-1.27 (t, J=3.4 Hz, 3H, CH2—CH3), 1.24-1.29 (t, J=7.1 Hz, 3H, CH2—CH3), 1.39-2.44 (broad m, 12H), 2.44-2.54 (dd, J=18.8 and 8.6 Hz, 1H), 2.77-2.83 (m, 2H), 3.84-3.87 (s, 3H, OMe), 5.0 (s, 2H, PhCH2), 6.6 (s, 1H, aromatic), 6.77 (s, 1H, aromatic), 3.87-3.84 (s, 3H, OMe), 4.10-4.16 (q, J=7.0 Hz, 2H, CH3—CH2—O), 5.09 (s, 2H, CH2-phenyl), 6.61 (s, 1H, 4-CH), 6.82 (s, 1H, aromatic 1-CH), 7.41-7.43 (m, 5H).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organics were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was pre-absorbed onto silica gel
  5. custompurified

Sources & evidence

ORD record
ord-d034b72548964ff4a8717d1660d6065d
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Linked notes

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