Diisopropylamine → 1-(4'-Decyloxybiphenyl-4-yl)-2-(1-hydroxy-1-methylethyl)ethyne

HRID 1250336Notes

Reaction equation

HRID 1250336 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:25][C:26]([OH:30])([C:28]#[CH:29])[CH3:27].C(NC(C)C)(C)C>C1COCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:29]#[C:28][C:26]([OH:30])([CH3:27])[CH3:25])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 106680514-Bromo-4'-decyloxybiphenyl

Product 1

HCID 183283931-(4'-Decyloxybiphenyl-4-yl)-2-(1-hydroxy-1-methylethyl)ethyne

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of compound 68 (15.00 g, 0.039 mol), 2-methylbut-3-yn-2-ol (7.15 g, 0.085 mol), copper(I) iodide (0.34 g, 1.80 mmol), tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.50 mmol) and diisopropylamine (150 ml) was heated under reflux in a dry nitrogen atmosphere for 24 h. The resultant mass was dissolved in THF and filtered over hyflo filter aid to remove inorganic materials. Volatile materials were removed in vacuo and the brown solid was recrystallised from ethanol to give a white, fluffy solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a dry nitrogen atmosphere for 24 h
  3. filtrationfiltered over hyflo
  4. filtrationfilter aid
  5. customto remove inorganic materials
  6. customVolatile materials were removed in vacuo
  7. customthe brown solid was recrystallised from ethanol
  8. customto give a white, fluffy solid

Sources & evidence

ORD record
ord-cd2ad2b4d6b54777837565dec498e068
Source dataset
uspto-grants-2002_01
Patent number
US06337420B1

Reaction notes

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