Ammonium Chloride → HCID 15703881, compound

HRID 1534376Notes

Reaction equation

HRID 1534376 reaction equation
[CH3:1][O:2][C:3]1[C:14]2[C:13](=[O:15])[O:12][CH2:11][C:10]3[CH:16]=[C:17]([CH3:22])[CH:18]=[C:19]([O:20][CH3:21])[C:9]=3[O:8][C:7]=2[CH:6]=[CH:5][C:4]=1[C:23](=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26].[CH3:29][Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[OH:28][C:23]([C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:9]3[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[CH:16][C:10]=3[CH2:11][O:12][C:13](=[O:15])[C:14]=2[C:3]=1[O:2][CH3:1])([CH3:29])[CH2:24][CH:25]([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15703848HCID 15703848, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 15703881HCID 15703881, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.26 mmol) of 4,11-dimethoxy-9-methyl-3-(3-methylbutan-1-onyl)-7H-dibenzo[b,g][1,5]dioxocin-5-one are dissolved in 5 ml of absolute tetrahydrofuran under argon and 0.2 ml (0.6 mmol) of a 3M methylmagnesium bromide solution in diethyl ether are added at room temperature. After 4 h, the reaction is discontinued by addition of 0.2 ml of ammonium chloride solution. The mixture is concentrated in vacuo, the residue is taken up in dichloromethane and the solution is washed with water. After drying the organic phase over magnesium sulphate, it is concentrated and the residue is purified by column chromatography on silica gel using petroleum ether/ethyl acetate 10:1.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washthe solution is washed with water
  3. dry with materialAfter drying the organic phase over magnesium sulphate, it
  4. concentrationis concentrated
  5. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5c5a3df82e2e4d43807eb94a8a219722
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

Loading…