Hydrochloric Acid → HCID 178498889, compound

HRID 1473275Notes

Reaction equation

HRID 1473275 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[Si]([CH:15]=[N+:16]=[N-:17])(C)(C)C.Cl>C1COCC1>[NH:16]1[CH:15]=[C:2]([C:3]([O:5][CH3:6])=[O:4])[C:1]([C:7]([O:9][CH3:10])=[O:8])=[N:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12980Dimethyl acetylenedicarboxylateHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 178498889HCID 178498889, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl acetylenedicarboxylate (1.73 mL, 14.07 mmol) in THF (65 mL) at 0° C. was added dropwise TMS-diazomethane (7.74 mL, 15.48 mmol, 2M/hexanes) and the mixture was allowed to warm to ambient temperature in 2 h. After 18 h, 1M hydrochloric acid (10 mL) was added until bubbling stopped and stirring at ambient temperature continued for 30 min. The mixture was diluted with EtOAc and washed with saturated sodium bicarbonate/water. The organic layer was dried over sodium sulfate and concentrated to provide the title compound as a yellowish solid (2.9 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.95 (s, 1H), 8.2 (s, 1H), 3.8 (s, 3H), 3.7 (s, 3H); ES-LCMS: 184.9 (M+1).

Workup

  1. customuntil bubbling
  2. waitcontinued for 30 min
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with saturated sodium bicarbonate/water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-097596b4545b46c1a741ea602347e5eb
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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