Ammonium Chloride → HCID 23353005, compound

HRID 1450118Notes

Reaction equation

HRID 1450118 reaction equation
C([Li])CCC.[CH2:6]([C:8]([O:15][CH2:16][O:17][CH3:18])([CH2:13][CH3:14])[CH2:9][CH2:10][C:11]#[CH:12])[CH3:7].[C:19]([O:27][CH:28]1[CH2:36][CH2:35][CH2:34][C:33]2([CH3:37])[CH:29]1[CH2:30][CH2:31][CH:32]2[C:38](=[O:40])[CH3:39])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[C:19]([O:27][CH:28]1[CH2:36][CH2:35][CH2:34][C:33]2([CH3:37])[CH:29]1[CH2:30][CH2:31][CH:32]2[C:38]([OH:40])([C:12]#[C:11][CH2:10][CH2:9][C:8]([CH2:13][CH3:14])([O:15][CH2:16][O:17][CH3:18])[CH2:6][CH3:7])[CH3:39])(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 23353004HCID 23353004, compoundHCID 23353009HCID 23353009, compoundHCID 178418339Butyllithium

Product 1

HCID 23353005HCID 23353005, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

0.32 ml of 1.6M hexane solution of butyl lithium was dropwise added to a solution of 120 mg of 5-ethyl-5-methoxymethoxy-1-heptyne dissolved in 4 ml of tetrahydrofuran, at -78° C. in a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 30 minutes. Thereto was dropwise added a solution of 112 mg of 4-benzoyloxy-7a-methyl-2,3,3a,4,5,6,7,7a-octahydroinden-1-yl-ethanone dissolved in 3 ml of tetrahydrofuran. The reaction mixture was warmed to 0° C. and mixed with an aqueous ammonium chloride solution. The mixture was subjected to extraction with diethyl ether. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 97 mg of 2-(4-benzoyloxy-7a-methyl-2,3,3a,4,5,6,7,7a-octahydroinden-1-yl)-7-ethyl-7-methoxymethoxy-3-nonyn-2-ol having the following properties.

Workup

  1. extractionThe mixture was subjected to extraction with diethyl ether
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b01d98c2cbf947618d5eac409fa1a52f
Source dataset
uspto-grants-1997_02
Patent number
US05600047

Reaction notes

Loading…