Ethyl vinyl ether → HCID 53882725, compound

HRID 1679196Notes

Reaction equation

HRID 1679196 reaction equation
[OH:1][N:2]=[C:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([O:6][CH3:7])=[O:5].[CH:13]([O:15][CH2:16][CH3:17])=[CH2:14]>C(OCC)(=O)C.P(Cl)(Cl)(Cl)=O>[CH2:13]([O:15][CH2:16][CH2:17][O:1][N:2]=[C:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([O:6][CH3:7])=[O:5])[CH3:14]

Participants

5

Reactant 2

HCID 8023Ethyl vinyl etherHCID 73676762HCID 73676762, compound

Product 1

HCID 53882725HCID 53882725, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of methyl 2-hydroxyimino-2-(thien-2-yl)acetate syn-isomer (3.98 g.) and ethyl vinyl ether (2.5 mls) in ethyl acetate (25 mls) was added phosphorous oxychloride (2 drops). After 20 mins. at 50° the ethyl acetate was washed with saturated sodium bicarbonate solution, dried over sodium sulphate and evaporated to an oil, giving methyl 2-(1 -ethoxy)ethoxyimino-2-(thien-2-yl)acetate (syn-isomer) (5.7 g; 100%) λmax. (EtOH) 289 nm (ε 11,700), τ (CDCl3 ; 60 MHz) 2.61 (multiplet; thienyl H5), 2.82 to 2.97 (multiplet; thienyl H3 and H4), 4.64 (quartet, J 5 Hz; ##STR58## 6.06 (singlet, -COOCH3), 6.24 (quartet, J 7 Hz, OCH2), 8.56 (doublet J 5 Hz; CH-CH3), 8.79 (triplet, J 7 Hz; O.(CH2CH3).

Workup

  1. washat 50° the ethyl acetate was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated to an oil

Sources & evidence

ORD record
ord-145034d934b24748a64204f558b62517
Source dataset
uspto-grants-1978_03
Patent number
US04079178

Reaction notes

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