Dimethyl Sulfoxide → HCID 12487496, compound

HRID 2352504Notes

Reaction equation

HRID 2352504 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][CH2:14][C:15]#[CH:16].C(N(CC)CC)C>C(Cl)Cl.O>[C:17]1([C:12]([CH2:13][CH2:14][C:15]#[CH:16])=[O:11])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1257135519082-37-2

Product 1

HCID 12487496HCID 12487496, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (7.0 mL, 76.6 mmol) in methylene chloride (200 mL) under argon atmosphere at -78° C. was added dropwise dimethylsulfoxide (11.9 mL, 152 mmol). After stirring for 15 minutes 1-hydroxy-1-phenylpent-4-yne (11.14 g, 69.6 mmol) in methylene chloride (20 mL) was added dropwise. After stirring at -78° C. for 1 hour triethylamine (48 mL, 340 mmol) was added and the orange reaction mixture was allowed to warm to room temperature. Water (100 mL) was added, the layers separated, and the organic extract was washed with 1% hydrochloric acid solution (4×100 mL), saturated sodium bicarbonate solution, brine, and dried (MgSO4). Evaporation of solvent under reduced pressure gave a solid which was recrystallized from petroleum ether to afford 5.25 g product. The mother liquors were distilled by Kugelrohr (80° C., 0.1 mm Hg) to give an additional 8.3 g (75 %) of product. 1H NMR (CDCl3) δ: 1.99 (t, J=2.69 Hz, 1H), 2.63 (t, J=7.21 Hz, 1H), 2.64 (t, J=6.17 Hz, 1H), 3.25 (t, J=6.23 Hz, 1H), 3.26 (t, J=7.20 Hz, 1H), 7.44-7.58 (m, 3H), 7.96-7.99 (m, 2H) ppm.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customthe layers separated
  4. extractionthe organic extract
  5. washwas washed with 1% hydrochloric acid solution (4×100 mL), saturated sodium bicarbonate solution, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of solvent under reduced pressure
  8. customgave a solid which
  9. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-ca15dad6c9244921b172a60c1d051355
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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