Diethyl Ether → HCID 21290722, compound

HRID 623224Notes

Reaction equation

HRID 623224 reaction equation
[Cl:1][C:2]1[S:6][CH:5]=[CH:4][CH:3]=1.[C:7]([O:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])#[C:8][CH3:9].C([N:20]([CH2:23]C)CC)C.C([O:27]CC)C>>[Cl:1][C:2]1[S:6][C:5]([C:23]2[CH:9]=[C:8]([CH2:7][O:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[O:27][N:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 72992-ChlorothiopheneHCID 8471TriethylamineHCID 57176700HCID 57176700, compound

Product 1

HCID 21290722HCID 21290722, compound

Procedure

A mixture of 4.9 g (25 mmol) of 5-chlorothiophene N-hydroxycarboximidoyl chloride and 4.54 g (27 mmol) of methyl 2-propynyloxy-2-methylpropionate in 180 ml of dry diethyl ether was treated with a solution of 2.53 g (25 mmol) of triethylamine in 20 ml of dry diethyl ether while stirring under nitrogen. After 3 days at 20° C. the mixture was filtered and the filtrate was evaporated to give 6.6 g of crude methyl 2-[[3-(5-chlorothien-2-yl)-5-isoxazolyl]methoxy]-2-methylpropionate in the form of an oil. 6.3 g of this oil, without further purification, were hydrolyzed in a manner analogous to that described in Example 12 to yield, after crystallization from ethyl acetate/hexane 2.1 g (28%) of 2-[[3-(5-chlorothien-2-yl)-5-isoxazolyl]methoxy]-2-methylpropionic acid of melting point 128°-130° C.

Workup

  1. filtrationAfter 3 days at 20° C. the mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-794aa831656c4f72b1cff494598f4de7
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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