3-Butyn-1-OL → HCID 66598264, compound

HRID 422473Notes

Reaction equation

HRID 422473 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[CH2:10]([OH:14])[CH2:11][C:12]#[CH:13]>>[F:9][CH2:8][C:4]1[N:3]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][OH:14])[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 135663-Butyn-1-OLHCID 102416102-Bromo-6-(fluoromethyl)pyridine2×

Product 1

HCID 66598264HCID 66598264, compoundYield 80.6%

Procedure

The title compound was prepared in accordance with the general method of Example 199(A), from 2-bromo-6-(fluoromethyl)pyridine (compound 190(E); 3.50 g, 18 mmol) and 3-butyn-1-ol (1.3 g, 18 mmol). The crude residue was purified over silicagel chromatography (prepacked 85 g silicagel column, DCM/MeOH: from 100/0 to 97/3 as eluent) to afford 2.60 g of 4-(6-(fluoromethyl)pyridin-2-yl)but-3-yn-1-ol as an orange solid (Yield: 79%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 85 g silicagel column, DCM/MeOH: from 100/0 to 97/3 as eluent)

Sources & evidence

ORD record
ord-63b651e0b9dd458c81aa9af7fdef12b9
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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