1,2-Dichloroethane → HCID 54487279, compound

HRID 1779949Notes

Reaction equation

HRID 1779949 reaction equation
[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH:18]=[C:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.[CH2:31]([O:33][CH2:34]Cl)[CH3:32].C(N(C(C)C)CC)(C)C.ClCCCl>C(OCC)(=O)C.CO>[CH2:31]([O:33][CH2:34][O:25][C@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C:19](=[CH:18][CH2:17][C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:27])[C@H:11]3[CH2:10][C@@H:8]3[O:9][C@@:5]4([O:29][CH2:30][C@H:2]([CH3:1])[CH2:3][CH2:4]4)[C@@H:6]([CH3:28])[C@@H:7]32)[CH2:24]1)[CH3:32]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 99474Diosgenin

Product 1

HCID 54487279HCID 54487279, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diosgenin (2.5 g, 6.0 mmol), chloromethyl ethyl ether (1.14 g, 12.0 mmol), diisopropylethylamine (3.90 g, 30.0 mmol) and 1,2-dichloroethane (75 mL) was stirred under nitrogen atmosphere at ambient temperature for 4 hours. Methanol (<1 mL) was added to quench the reaction. The mixture was diluted with ethyl acetate and washed with water (2x), brine (1x), dried over sodium sulfate, filtered and concentrated in vacuo to give 2.17 g (76.5%) of the title compound as a colorless solid.

Workup

  1. customto quench
  2. customthe reaction
  3. washwashed with water (2x), brine (1x)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1589102508349229ed6f7bb577bb520
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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