Diethyl Ether → (1-phenyl-1H-1,2,3-triazol-4-yl)methanol

HRID 628676Notes

Reaction equation

[C:1]1([N:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)C.[CH2:15]([OH:18])[C:16]#[CH:17]>>[C:1]1([N:7]2[CH:17]=[C:16]([CH2:15][OH:18])[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 7859Propargyl alcohol

HCID 69319Azidobenzene

Product 1

HCID 708707(1-phenyl-1H-1,2,3-triazol-4-yl)methanolYield 35%

Conditions

Temperature: 90 °C

Procedure

Phenyl azide (2.02 g, 17.0 mmol) was dissolved in neat propargyl alcohol (3 mL) and the mixture was heated to 90° C. for 2 h. The reaction mixture was cooled to room temperature and the reaction mixture was diluted into diethyl ether and left overnight during which time 7 precipitated as a crystalline solid to afford 1.03 g (35%) of the desired product 7 while the mother liquor contained primarily the regioisomer 9: 1H NMR (400 MHz, CDCl3) δ 7.97, (s, 1H), 7.70, (d, J=8.40 Hz, 2H), 7.50, (m, 2H), 7.41 (m, 1H), 4.88, (d, J=6.00 Hz, 2H), 2.70, (bs, 1H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customprecipitated as a crystalline solid

Sources & evidence

ORD record: ord-f66d69fdc37f4986a442454191e7da29
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09314468B2

Reaction notes

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