Benzene → HCID 18621499, compound

HRID 1861785Notes

Reaction equation

HRID 1861785 reaction equation
[CH2:1]([OH:6])[C:2]#[C:3][CH2:4]O.[CH:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH:28](Cl)(Cl)Cl>>[C:19]([O:6][CH2:1][C:2]#[C:3][CH2:4][N:13]1[CH2:18][CH2:17][CH:16]([CH2:28][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 1049PyridineHCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 80662-Butyne-1,4-diol

Product 1

HCID 18621499HCID 18621499, compoundYield 10%

Procedure

To a solution of but-2-yne-1,4-diol (19 g, 0.22 mol) in a mixture of dry benzene (50 mL) and dry pyridine (22 mL) was added dropwise a solution of benzoyl chloride (22 mL) in dry chloroform (40 mL) at 0-5° C. The resulting solution was allowed to stir at room temperature for another 4 hr and was washed with 1 N H2SO4 (4×20 mL), water (3×20 mL) and was dried over Na2SO4. Evaporation of solvent gave a residue, which was purified by flash chromatography to give the title compound as a colorless oil (3.5 g, 10%): 1H NMR (CDCl3) d 1.74 (bs, 1 H), 4.34 (s, 2 H), 4.97 (s, 2 H), 7.45 (m, 2 H), 7.56 (m, 2 H), 8.06 (d, J=7.5 Hz, 2 H).

Workup

  1. washwas washed with 1 N H2SO4 (4×20 mL), water (3×20 mL)
  2. dry with materialwas dried over Na2SO4
  3. customEvaporation of solvent
  4. customgave a residue, which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-5c0f753ffde948b69c766607c24a40da
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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