Chloromethyl Methyl Ether → HCID 86749912, compound

HRID 864506Notes

Reaction equation

HRID 864506 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([OH:35])[C@H:12]([OH:34])[C@@H:13]([CH2:15][O:16][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[O:14][C@H:8]3[N:7]([CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[C:6]=2[CH:43]=1.[O:44]1[CH2:48]CC[CH2:45]1.CN(C)C=O.[H-].[Na+].Cl[CH2:57][O:58][CH3:59]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:35][CH2:57][O:58][CH3:59])[C@H:12]([O:34][CH2:45][O:44][CH3:48])[C@@H:13]([CH2:15][OH:16])[O:14][C@H:8]3[N:7]([CH2:36][CH2:37][N:38]([CH2:39][CH3:40])[CH2:41][CH3:42])[C:6]=2[CH:43]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 131719598HCID 131719598, compound

Product 1

HCID 86749912HCID 86749912, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 3.00 g of the compound (24) obtained in Example 23 in 50 ml of a mixed solution of tetrahydrofuran-dimethylformamide (4:1), 600 mg of 60% oily sodium hydride and 1.17 ml of chloromethylmethyl ether were added, and the mixture was stirred for two hours at room temperature. The reacted solution was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated aqueous sodium chloride successively, and was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the solution of the resulting crude material in 75 ml of tetrahydrofuran, 9 ml of a 1M tetrabutylammoniumfluoride-tetrahydrofuran was added, and the solution was stirred overnight at room temperature. The reaction solution was concentrated, the residue was dissolved in ethyl acetate, and the solution was washed with water, and saturated chloride successively. The organic layer aqueous sodium was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and saturated aqueous sodium chloride successively
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. additionTo the solution of the resulting crude material in 75 ml of tetrahydrofuran, 9 ml of a 1M tetrabutylammoniumfluoride-tetrahydrofuran was added
  6. stirringthe solution was stirred overnight at room temperature
  7. concentrationThe reaction solution was concentrated
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washthe solution was washed with water, and saturated chloride successively
  10. dry with materialThe organic layer aqueous sodium was dried over anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1d42fe1f448a49e09500290acf0bb118
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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