Sodium Hydroxide → HCID 58568485, compound

HRID 634045Notes

Reaction equation

HRID 634045 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[C:9]([C:19]#[C:20][Si](C)(C)C)[CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>CO.CCCCCCC.C(OCC)(=O)C>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[C:9]([C:19]#[CH:20])[CH:8]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68649922HCID 68649922, compound

Product 1

HCID 58568485HCID 58568485, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

Sodium hydroxide (1N) was added to the crude (4-tert-butyl-1,2-phenylene)bis(ethyne-2,1-diyl)bis(trimethylsilane) in methanol to remove the trimethylsilane groups. Stirring for 30 minutes resulted in the crude final product mixture. Column chromatography using heptane:ethyl acetate (99:1) as eluent provided the desired compound, 4-tert-butyl-1,2-diethynylbenzene, as a brown oil (1.08 g, 5.9 mmol). 1H-NMR (CDCl3) δ 1.30 (s, 9H) 3.28 (s, 1H) 3.30 (s, 1H) 7.33 (d, 1H) 7.43 (d, 1H) 7.51 (d, 1H)

Workup

  1. customto remove the trimethylsilane groups
  2. customresulted in the crude final product mixture

Sources & evidence

ORD record
ord-4bf657a4373c41e8a3ee6f4221813c2a
Source dataset
uspto-grants-2016_04
Patent number
US09321896B2

Reaction notes

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