Boron trifluoride → HCID 13588518, compound

HRID 1284441Notes

Reaction equation

HRID 1284441 reaction equation
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].B(F)(F)F>C(O)(CC)C.CCOCC>[C:1]([O:16][CH:2]([CH2:3][CH3:4])[CH3:1])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 6356Boron trifluorideHCID 53127097-Tetradecynoic acid

Product 1

HCID 13588518HCID 13588518, compoundYield 170.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A solution of 7-tetradecynoic acid (1.22 g) and BF3 -etherate (1 ml) in 20 ml of sec-butyl alcohol was refluxed for 18 hours. The solution was diluted with ether and washed with saturated Na2CO3 solution, water, 2N NaOH, water, and saturated NH4Cl solution. The ether layer was dried (MgSO4) and the solvent removed under reduced pressure to give 1.30 g of sec-butyl 7-tetradecynoate as a yellow liquid.

Workup

  1. washwashed with saturated Na2CO3 solution, water, 2N NaOH, water, and saturated NH4Cl solution
  2. dry with materialThe ether layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0ae7ca54a92c4c50b37642c9ed474bc5
Source dataset
uspto-grants-1986_01
Patent number
US04563348

Reaction notes

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