Diethyl Ether → HCID 10013562, compound

HRID 1758591Notes

Reaction equation

HRID 1758591 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][Si](C)(C)C)=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)(C)C.C(OCC)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:21]#[C:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]#[CH:5])=[CH:12][CH:11]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12687364HCID 12687364, compound2×

Product 1

HCID 10013562HCID 10013562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In Step III, a suspension of 1.00 g (2.78 mmoles) of bis(4-trimethylsilylethynylphenyl) methane [Compound (4)] in 50 ml anhydrous deaerated methanol was treated with enough anhydrous ethyl ether to dissolve all solid particles at 25° C. Anhydrous potassium carbonate (300 mg) was added and the mixture was stirred at 25° C. under argon for 16 hours. The solvent was removed and the solid residue was dissolved in 50 ml dichloromethane, treated with 5 g of silica gel and evaporated to dryness. The powder was placed on top of a 40-cm (I.D. 30 mm) column of silica gel (EM Labs, 70-230 mesh) and the column was developed with passage of hexane. A crystalline white solid [Compound (6)] was recovered from the the eluate: 0.60 gm (2.78 mmoles, 100%); mp 63°-64° C. After drying at 56° C./0.01 mm Hg inside an Abderhalden apparatus for 2 hours, the mp increased to 65.5°-66.5° C. IR (KBr) 3280 (very strong, sharp, --C≡CH), 2100 (weak, sharp, --C≡C--), and 1500 cm-1 (medium, sharp, C=C); MS (70 eV) m/e 216 (molecular ion); NMR (CDCl3) δ3.03 (s,2H,C≡C--H), 3.95(s,2H,CH2), 7.10 and 7.43 ppm (q,8H, JAB =8.0 Hz, aromatic).

Workup

  1. dissolutionto dissolve all solid particles at 25° C
  2. customThe solvent was removed
  3. dissolutionthe solid residue was dissolved in 50 ml dichloromethane
  4. additiontreated with 5 g of silica gel
  5. customevaporated to dryness
  6. customA crystalline white solid [Compound (6)] was recovered from the the eluate
  7. customAfter drying at 56° C./0.01 mm Hg inside an Abderhalden apparatus for 2 hours
  8. temperaturethe mp increased to 65.5°-66.5° C

Sources & evidence

ORD record
ord-8814ed13da61491f832581bcc60464c6
Source dataset
uspto-grants-1983_02
Patent number
US04374291

Reaction notes

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