Hexane → t-Butyl{[2-chloro-4-(trifluoromethyl)-5-thiazolyl]methoxy}acetate

HRID 354726Notes

Reaction equation

HRID 354726 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].CCCCCC.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[C:18]([O:17][C:15](=[O:16])[CH2:14][O:12][CH2:11][C:4]1[S:3][C:2]([Cl:1])=[N:6][C:5]=1[C:7]([F:8])([F:9])[F:10])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 8058HexaneHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 12953359(2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

Product 1

HCID 12953368t-Butyl{[2-chloro-4-(trifluoromethyl)-5-thiazolyl]methoxy}acetateYield 16.6%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 4.32 G (0.02 Mol) of the compound of Example 4, 0.1 g of Aliquat 336, 3.9 g of t-butyl bromoacetate, 50 ml of hexane, 10 g of sodium hydroxide and 24 ml of water was held at reflux for 1 hour. The reaction mixture was filtered. The hexane layer was separated, dried over MgSO4 and concentrated under reduced pressure. The residue (1.6 g) was chromatographed on silica gel using ether-petroleum ether (2:98 v/v) as eluant. The first fraction gave 1.1 g (16.5%) of t-butyl{[2-chloro-4-(trifluoromethyl)-5-thiazolyl]methoxy}acetate, as an oil, nD25 1.4607.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. customThe hexane layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue (1.6 g) was chromatographed on silica gel

Sources & evidence

ORD record
ord-35a0c830bdd146d78e0a8b5826d6ae2b
Source dataset
uspto-grants-1983_03
Patent number
US04377054

Reaction notes

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