Hydrochloric Acid → HCID 117772618, compound

HRID 2281092Notes

Reaction equation

HRID 2281092 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]=[O:8])[O:4][N:3]=1.[F-].[Cs+].C[Si](C)(C)[C:13]([F:16])([F:15])[F:14].Cl>C1COCC1.O>[F:14][C:13]([F:16])([F:15])[CH:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)[OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 105827583-Methyl-1,2-oxazole-5-carbaldehyde

Product 1

HCID 117772618HCID 117772618, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

A mixture of 0.1 g (0.9 mmol) 3-Methyl-isoxazole-5-carbaldehyde and 14 mg (0.09 mmol) CsF and THF is cooled to −5° C. 540 μl (1.1 mmol) trimethyl(trifluormethyl)-silane 2 M in THF is added dropwise and after 30 min the mixture is allowed to reach RT. After cooling with ice and addition of 5 ml 1 N aq. HCl, the mixture is stirred at RT over night, diluted with water and extracted with DCM. The combined organic layers are dried and evaporated giving rise to 2,2,2-trifluoro-1-(3-methylisoxazol-5-yl)ethanol.

Workup

  1. customto reach RT
  2. extractionextracted with DCM
  3. customThe combined organic layers are dried
  4. customevaporated

Sources & evidence

ORD record
ord-1aecc5926bde4e89855692662c9bba99
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

Loading…