1,2-Dichloroethane → HCID 54487279, compound

HRID 1941186Notes

Reaction equation

HRID 1941186 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), chioromethyl 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 (2×), brine (1×), 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 (2×), brine (1×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3c2b3c378c84ff78e8d3e3f4bd7e29c
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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