Methyl iodide → HCID 70542166, compound

HRID 1156039Notes

Reaction equation

HRID 1156039 reaction equation
[CH3:1][N:2]([CH3:24])[N:3]=[C:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]12[CH3:6])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3.[CH2:25]([Li])CCC.CI.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:24][N:2]([CH3:1])[N:3]=[C:4]1[C@H:9]([CH3:25])[CH2:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]12[CH3:6])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 56622881HCID 56622881, compoundHCID 178418339Butyllithium

Product 1

HCID 70542166HCID 70542166, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5 g of 3-methoxy-1,3,5(10)-estratrien-17-one N,N-dimethylhydrazone in 50 ml of absolute tetrahydrofuran (THF) is combined dropwise at 0° C. with 13 ml of a 15% solution of n-butyllithium in hexane. After this addition the mixture is stirred for 60 minutes under argon at 0° C., then 1.3 ml of methyl iodide is added dropwise thereto at 0° C., and the mixture is stirred for another 30 minutes at room temperature. To work up the mixture, it is poured into saturated ammonium chloride solution and extracted with ethyl acetate. Crystallization from acetonitrile yields 5 g of 3-methoxy-16α-methyl-1,3,5(10)-estratrien-17-one N,N-dimethylhydrazone, m.p. 122°-124° C.

Workup

  1. additionAfter this addition the mixture
  2. stirringat 0° C., and the mixture is stirred for another 30 minutes at room temperature
  3. extractionextracted with ethyl acetate
  4. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-1df8caa9849f4b16956700a629409c22
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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