Diethyl Ether → HCID 57756688, compound

HRID 227660Notes

Reaction equation

HRID 227660 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:19]([O:21]CC)=[O:20])=[C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[N:6]=1.[Li+].[OH-].[OH-].[Na+].C(OCC)C>O1CCCC1>[Cl:1][C:2]1[S:3][C:4]([C:19]([OH:21])=[O:20])=[C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:17])([F:16])[F:18])[N:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 57756680HCID 57756680, compound

Product 1

HCID 57756688HCID 57756688, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxylate (0.535 g, 1.46 mmol) was dissolved in 15 mL of tetrahydrofuran with stirring, and 15 mL of 1N LiOH solution was added via pipet. The mixture was stirred for 18 hours, and poured into 0.1 N NaOH and diethyl ether. The layers were separated, and the aqueous layer was acidified to pH 2 with concentrated HCl. The mixture was filtered and the white solid was washed with water. The solid was air dried, collected, and dried further under vacuum to yield 0.418 g (85%) of 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ 13.22 (br s, 1H), 7.83-7.70 (m, 3H), 7.58 (m, 1H), 5.59 (s, 2H).

Workup

  1. stirringThe mixture was stirred for 18 hours
  2. customThe layers were separated
  3. filtrationThe mixture was filtered
  4. washthe white solid was washed with water
  5. customdried
  6. customcollected
  7. customdried further under vacuum

Sources & evidence

ORD record
ord-ec9afac0058941cb9d9a93c7a17f9386
Source dataset
uspto-grants-2009_07
Patent number
US07560568B2

Reaction notes

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