Methanol → Bis(4-ethynylphenyl)acetylene

HRID 556139Notes

Reaction equation

HRID 556139 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][Si](C)(C)C)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)C.CO.[OH-].[K+]>C(Cl)Cl>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]#[C:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]#[CH:5])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1)#[CH:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 59806151HCID 59806151, compound

Product 1

HCID 12160828Bis(4-ethynylphenyl)acetyleneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Subsequently, the obtained 4,4′-bis(trimethylsilylethynyl)tolan (149 mg, 0.40 mmol) was added with dist. CH2Cl2 (5 mL), dist. MeOH (1 mL) and an aqueous solution of KOH of 50% by mass (0.09 mL). The resultant mixture was then stirred under a nitrogen atmosphere at room temperature for 18 hours to obtain a reaction mixture. After that, the reaction mixture was diluted with CH2Cl2. The organic layer was washed with sat. NaCl, and the washed organic layer was dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product (II). Subsequently, the obtained crude product (II) was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 4,4′-diethynyltolan (60.5 mg, 86% yield (in two steps)).

Workup

  1. customto obtain a reaction mixture
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialthe washed organic layer was dried with MgSO4
  4. filtrationThe dried organic layer was filtered
  5. concentrationconcentrated
  6. customto obtain a crude product (II)
  7. customSubsequently, the obtained crude product (II)
  8. customwas separated
  9. custompurified by silica gel column chromatography (hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-5cecf5c576274800b78f800763ee66c1
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

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