Benzyl Bromide → HCID 10549342, compound

HRID 369511Notes

Reaction equation

HRID 369511 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]1[C:13]([OH:31])=[CH:14][C:15]2[CH2:16][CH2:17][C@@H:18]3[C@@H:27]([C:28]=2[CH:29]=1)[CH2:26][CH2:25][C@@:23]1([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]1[OH:30])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:9]([O:11][C:12]1[C:13]([O:31][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:15]2[CH2:16][CH2:17][C@@H:18]3[C@@H:27]([C:28]=2[CH:29]=1)[CH2:26][CH2:25][C@@:23]1([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]1[OH:30])[CH3:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 383045HCID 383045, compound

Product 1

HCID 10549342HCID 10549342, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Benzyl bromide (4.5 g, 38 mmol) was added to a suspension of 2-ethoxy-β-estra-3,17β-diol (2) (4.5 g, 13 mmol) and potassium carbonate (8.6 g, 62 mmol) in anhydrous ethanol (100 mL) under argon atmosphere at 0° C. The resulting mixture was stirred at 100±5° C. for 7-8 h. The solvent was evaporated under reduced pressure and the residue was diluted with water, and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic solution was washed with water (100 mL), sodium bicarbonate (120 mL), brine (100 mL), and dried over sodium sulfate. The ethyl acetate layer on evaporation under reduced pressure gave a viscous oil (5.8 g), which was used as such without any further purification in the next step: 1H NMR, (CDCl3) δ 7.35 (s, 5 H), 6.75 (s, 1 H) 6.65 (s, 1 H), 5.5 (s, 1 H), 4.55 (s, 2 H), 4.04 (q, J=6.4, 2 H), 3.5 (t, J=8.5 Hz, 1 H), 2.75 (m, 3 H), 2.20-1.95 (m, 6 H), 1.90-1.80 (m, 2 H), 1.75-1.5 (m, 2 H), 1.45-1.1 (m, 7 H, 0.85 (s, 1 H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate (3×200 mL)
  4. washThe combined organic solution was washed with water (100 mL), sodium bicarbonate (120 mL), brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe ethyl acetate layer on evaporation under reduced pressure

Sources & evidence

ORD record
ord-3d90430eff70488ea9f921e7cd22ba82
Source dataset
uspto-grants-2000_10
Patent number
US06136992

Reaction notes

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