Propargyl alcohol → 5-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)

HRID 2189496Notes

Reaction equation

HRID 2189496 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:15])([F:14])/[C:10](/Br)=[N:11]/[OH:12].[CH2:16]([OH:19])[C:17]#[CH:18]>C1(C)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[C:10]1[CH:18]=[C:17]([CH2:16][OH:19])[O:12][N:11]=1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 13307986HCID 13307986, compound

Product 1

HCID 133079935-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)Yield 58.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of triethylamine (5.35 ml, 38.6 mmol) in toluene (15 ml) was added dropwise over 10 minutes to a solution of (Z)-2,2,2-trifluoro-N-hydroxyacetimidoyl bromide (71) (5.35 g, 19.3 mmol) and prop-2-yn-1-ol (72) (3.25 g, 57.9 mmol, TCI_JP) in toluene (37.5 ml) and stirred for 10 hours at room temperature. The reaction was quenched with H2O (30 ml), extracted with ethyl acetate (50 ml), washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a crude product of (3-(trifluoromethyl)isoxazol-5-yl)methanol (73) (1.88 g, yield 47%) as a brown oil.

Workup

  1. customThe reaction was quenched with H2O (30 ml)
  2. extractionextracted with ethyl acetate (50 ml)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76b45eb2555b42338e5555580a653cd2
Source dataset
uspto-grants-2012_12
Patent number
US08324249B2

Reaction notes

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