Ammonium Chloride → HCID 14851366, compound

HRID 2082190Notes

Reaction equation

HRID 2082190 reaction equation
[CH:1]([C@H:3]1[C@@H:8](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[CH:13]([O:22][C:23](=[O:25])[CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:7][CH:6]=[CH:5][CH2:4]1)=[O:2].[Cl-].[NH4+]>O1CCCC1.[Mg]>[C:1]([O:2][CH:1]([C@H:3]1[C@@H:8](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[CH:13]([O:22][C:23](=[O:25])[CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:7][CH:6]=[CH:5][CH2:4]1)[CH2:10][CH2:11][CH2:12][CH2:13][OH:22])(=[O:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 14851357HCID 14851357, compound

Product 1

HCID 14851366HCID 14851366, compoundYield 146.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5462224MagnesiumSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 4.2 g of cis-(1RS)-1-formyl-(6RS)-6-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-3-cyclohexene in 8.25 ml of tetrahydrofuran is installed in 29.9 ml of this magnesium organic solution at -20° C. under argon and stirred for 30 minutes at -20° C. It is mixed with 150 ml of saturated ammonium chloride solution, extracted three times with ether, the organic phase is shaken out with brine, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/ethyl acetate (8+2), 4.1 g of the alcohol is obtained as a colorless oil.

Workup

  1. extractionextracted three times with ether
  2. stirringthe organic phase is shaken out with brine
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-4aa11551949f419f9cda248915b1efdb
Source dataset
uspto-grants-1993_02
Patent number
US05187286

Reaction notes

Loading…