Diethyl Ether → HCID 13621582, compound

HRID 1721982Notes

Reaction equation

HRID 1721982 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][CH:13]([OH:16])[CH2:14]O)=[CH:9][CH:8]=1.N1C=CC=CC=1.Cl.CS(Cl)(=O)=O.CCOCC>O.CO.N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][CH:13]2[O:16][CH2:14]2)=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 10176127Pyridinium chlorideHCID 13621581HCID 13621581, compound

Product 1

HCID 13621582HCID 13621582, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Into a flask under N2 was placed 6 (7.0 g, 0.03 mol), pyridine (20 ml), pyridine·HCl (3.9 g, 0.034 mol) and the mixture cooled in an ice bath. To the cooled mixture was added methanesulfonyl chloride (3.26 g, 2.2 ml, 0.028 mol). After 10 minutes, Et2O (130 ml) NaOCH3 (19 g, 0.35 mol), and CH3OH (65 ml) were added and the suspension stirred for 1/2 hour. Water was added and the layers were separated. The aqueous layer was further extracted with CH2Cl2 (3X). The combined extracts were washed with H2O, saturated NaCl, dried, filtered and concentrated to dryness to yield 7; 'H NMR (CDCl7) δ 2.8 (2H, m), 3.3 (1H, m), 3.65 (3H, s), 4.1 (2H, m), 7.4 (6H, m).

Workup

  1. customInto a flask under N2 was placed
  2. customthe layers were separated
  3. extractionThe aqueous layer was further extracted with CH2Cl2 (3X)
  4. washThe combined extracts were washed with H2O, saturated NaCl
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customto yield 7

Sources & evidence

ORD record
ord-2b6eb8e1fd9543e9aec2bca5491be1fa
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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