Potassium Carbonate → Dibenzyl ether

HRID 1675909

반응식

HRID 1675909 반응식
[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

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 4406242-Methoxyestrone

생성물 1

HCID 7657Dibenzyl ether수율 379.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d034b72548964ff4a8717d1660d6065d
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003783B2

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