Diethyl Ether → HCID 20452089, compound

HRID 355252Notes

Reaction equation

HRID 355252 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[N-:11]=[N+:12]=[N-:13].[Na+].CCCCCC.CCOCC>CN(C=O)C.O>[N:11]([CH2:2][CH2:3][O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:12]=[N-:13]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 33557Sodium AzideHCID 10964894Ethyl 2-(2-chloroethoxy)acetate

Product 1

HCID 20452089HCID 20452089, compoundYield 114%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-chloroethoxyacetate (7.71 g, 36.3 mmol) and sodium azide (3.31 g, 50.9 mmol) in DMF (100 ml) was heated at 80°-90° C. for 3.5 h by which time tlc (hexane; ether 1:1) indicated that the reaction was complete. The cooled mixture was poured into H2O (1 l) and extracted with ether (250 ml×3). The extracts washed with H2O (×2) and brine (×1) were dried (MgSO4) and evaporated yielding 7.16 g (41.4 mmol 89.4%) of ethyl 2-azidoethoxyacetate as a yellowish oil: 1Hmr (CDCl3) δ: 1.30 (3H, t, J=7 Hz, --OCH2CH3), 3.3-4.0 (4H, m, --OCH2CH2N3), 4.13 (2H, s, --COCH2O--), 4.23 ppm (2H, q, J=7 Hz, --OCH2CH3); ir (neat) νmax : 2100 (N3) and 1750 cm-1 (C=O ester). This material was used in the next step without further purification.

Workup

  1. extractionextracted with ether (250 ml×3)
  2. washThe extracts washed with H2O (×2) and brine (×1)
  3. dry with materialwere dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-7650dcfa6df0489baa15db3a976f5911
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

Loading…