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

HRID 1757914Notes

Reaction equation

HRID 1757914 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>[Cl:1][C:2]1[S:3][C:4]([CH2:11][O:12][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

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-fc1a838099ea454f9f874ad87e4e164b
Source dataset
uspto-grants-1983_02
Patent number
US04371389

Reaction notes

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