Ammonium Chloride → HCID 70615461, compound

HRID 2083793Notes

Reaction equation

HRID 2083793 reaction equation
[CH3:1][Mg]I.[CH2:4]([O:6][C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[C:18](=[CH:19][CH2:20][C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:16][C@H:15]1[OH:28])[CH3:5].[NH4+].[Cl-]>C(OCC)C>[CH2:4]([O:6][C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[C:18](=[CH:19][CH2:20][C:21]([OH:27])([CH3:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:16][C@H:15]1[OH:28])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 54372282HCID 54372282, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 70615461HCID 70615461, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methyl magnesium iodide (prepared from 816 mg. magnesium filings and 2.12 ml. methyl iodide) dissolved in 80 ml. dry diethyl ether is added dropwise to 3.9 g. 9β-hydroxy-15-oxo-12-prostenoic acid ethyl ester, dissolved in 200 ml. dry diethyl ether, with the exclusion of moisture, under nitrogen and with stirring. The mixture is stirred for 15 minutes more at room temperature and mixed dropwise, with ice cooling, with 300 ml. saturated aqueous NH4Cl solution. The organic phase is separated, washed with water and dried over Na2SO4. The solvent is removed by distillation to yield as residue 9β,15-dihydroxy-15-methyl-12-prostenoic acid ethyl ester, which is separated chromatographically (first silica gel/dichloromethane:acetone = 10:1; then silica gel/petroleum ether:ethanol = 9:1) into the two 15-epimers;

Workup

  1. additionmixed dropwise, with ice cooling, with 300 ml
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed by distillation

Sources & evidence

ORD record
ord-0b7e10d184404845942b7b7c7477a0b3
Source dataset
uspto-grants-1978_04
Patent number
US04086362

Reaction notes

Loading…