Diisopropyl Ether → HCID 20337244, compound

HRID 1706179Notes

Reaction equation

HRID 1706179 reaction equation
[CH2:1]([O:8][N:9]([CH2:20][CH2:21]Br)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].C(OCC)(=O)C.C(OC(C)C)(C)C>O>[CH2:1]([O:8][N:9]([CH2:20][CH2:21][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 20337232HCID 20337232, compound

Product 1

HCID 20337244HCID 20337244, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of N-benzyloxy-N-(2-bromoethyl)-p-toluenesulfonamide (16.2 g.) and triethyl phosphite (21.0 g.) was stirred at 160° C. for 10 hours and then cooled to ambient temperature. To the reaction mixture was added ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give an oily residue (20.5 g.). A small volume of isopropyl ether was added to the residue to give crystals, which was separated by filtration and dried to give crystalline diethyl 2-(N-benzyloxy-N-tosylamino)ethylphosphonate (10.6 g.). The object compound (2.1 g.) was also recovered from the mother liquor by subjecting to a column chromatography on silicagel (developing solvent: chloroform)

Workup

  1. temperaturecooled to ambient temperature
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oily residue (20.5 g.)
  7. customto give crystals, which
  8. customwas separated by filtration
  9. customdried

Sources & evidence

ORD record
ord-38e31f6c3b0240cca7b7b8ad96c7b7c2
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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