Estrone → HCID 22983877, compound

HRID 1263483Notes

Reaction equation

HRID 1263483 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:44][CH2:45][O:46][CH3:47]>CC#N>[CH3:47][O:46][CH2:45][CH2:44][O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 5870EstroneHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 1859152-Naphthylalanine

Product 1

HCID 22983877HCID 22983877, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of estrone (10 g; 37 mmol), Nal (1.1 g, 7.4 mmol), Cs2CO3 (18.08 g; 55.5 mmol) and Br(CH2)2OCH3 (15 mL; 156 mmol) in CH3CN (200 mL) was refluxed for 1 h. The mixture was filtered over silica gel and washed successively with CH2Cl2 and EtOAc to give the ether (12.1 g; 99.4%); 1H NMR (300 MHz, CDCl3) δ 7.23 (d, 1H, J=8.6 Hz), 6.75 (dd, 1H, J=2.6, 8.6 Hz), 6.72 (s, 1H), 4.1 (t, 2H, J=4.4 Hz), 3.74(t, 2H, J=3.7 Hz), 3.44 (s, 3H), 2.87 (dd, 2H, J=4.25, 8.5 Hz), 2.48 (dd, 1H, J=8.4, 18.7 Hz), 0.91 (s, 3H).

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationThe mixture was filtered over silica gel
  3. washwashed successively with CH2Cl2 and EtOAc
  4. customto give the ether (12.1 g; 99.4%)

Sources & evidence

ORD record
ord-ca5f4d955a034c1c850100799ba6ff4b
Source dataset
uspto-grants-2003_04
Patent number
US06541463B1

Reaction notes

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