Acetylene → 1-(4-Fluorophenoxy)but-3-yn-2-ol

Acetylene gas, dried by passing through a trap containing sulfuric acid, is bubbled at a moderate rate, through 5 ml of vigorously stirred tetrahydrofuran, for 15 minutes. To this acetylenic solution, is then added dropwise, with continued passage of acetylene, 3.5 ml of a 2.4M solution of n-butylmagnesium chloride in tetrahydrofuran (8.4 mmoles) over 45 minutes. The mixture is stirred a further 15 minutes, and a solution of 580 mg (3.9 mmoles) of p-fluorophenoxy acetaldehyde (Example 156) in 3 ml of tetrahydrofuran is added dropwise over 15 minutes. This solution is stirred for 2 more hours, with passage of acetylene, poured into 50 ml of a saturated solution of ammonium chloride, extracted twice with 50 ml of ether, washed with 10 ml of ammonium chloride solution, dried with magnesium sulfate, filtered, and evaporated. The crude subject product is purified by sublimation at 75° C. (0.1 mm) for 5 hours to give 330 mg (48%) of white crystals, mp 46°-47° C.

1. dry with materialAcetylene gas, dried
2. customby passing through a trap
3. additioncontaining sulfuric acid
4. customis bubbled at a moderate rate, through 5 ml of vigorously stirred tetrahydrofuran, for 15 minutes
5. extractionextracted twice with 50 ml of ether
6. washwashed with 10 ml of ammonium chloride solution
7. dry with materialdried with magnesium sulfate
8. filtrationfiltered
9. customevaporated
10. customis purified by sublimation at 75° C. (0.1 mm) for 5 hours

ORD record

ord-d01580ce8073403d96de8399bac033b1

Source dataset

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04154954