Iodoethane → HCID 69884098, compound

HRID 2121345Notes

Reaction equation

HRID 2121345 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:22]([OH:23])=[CH:21][C@H:20]2[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][CH2:25][O:26][CH3:27])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:35][CH3:36]>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:22]([O:23][CH2:35][CH3:36])=[CH:21][C@H:20]2[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][CH2:25][O:26][CH3:27])[CH:6]=1

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 69884302HCID 69884302, compound

Product 1

HCID 69884098HCID 69884098, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,17β-bis(methoxymethoxy)estra-1,3,5-triene-2-ol (Z. Wang and Cushman, Synzthetic Commun. 28:4431-4437 (1998)) (11.3 g, 27.8 mmol) in anhydrous ethanol (225 ml) containing anhydrous potassium carbonate (38.4 g, 280 mmol) was stirred at room temperature under argon for 10 min. Iodoethane (43.7 g, 280 mmol) was introduced to the reaction mixture. The resulting mixture was stirred at gentle reflux. After 4 hr, another portion of iodoethane (10.92 g, 70 mmol) was introduced and the reflux was continued for another 10 hr. The reaction mixture was cooled to room temperature and filtered. The solid was washed with ether (100 ml), and the filtrates were combined and evaporated to dryness. Chromatography of the residue (silica gel 230-400 mesh, ethyl acetate:hexane 1:7 by volume) gave the pure 2 (10.45 g, 92%) as a colorless oil: 1H NMR (CDCl3) δ6.85 (s, 2 H), 5.18 (s, 2 H), 4.66 (ABq, J=6.6 Hz, Δν=3.4 Hz, 2 H), 4.08 (q, J=7.0 Hz, 2 H), 3.61 (t, J=8.5 Hz, 1 H), 3.52 (s, 3 H), 3.38 (s, 3 H), 2.79 (m, 2 H), 2.30-1.20 (m, 13 H), 0.82 (s, 3 H); CIMS (isobutane) m/z (rel intensity) 405 (MH+, 39), 343 (100). Anal. Calcd. for C24H37O5: C, 71.26; H, 8.97. Found: C, 71.48; H, 9.14.

Workup

  1. stirringThe resulting mixture was stirred at gentle reflux
  2. waitAfter 4 hr
  3. waitthe reflux was continued for another 10 hr
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationfiltered
  6. washThe solid was washed with ether (100 ml)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a3bc1b212b8c43a0888ffc9842d486f8
Source dataset
uspto-grants-2004_02
Patent number
US06696436B1

Reaction notes

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