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2-Methyl-3-butyn-2-ol → 4-[4-(6-Methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol

HRID 1816687
Notes
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Reaction equation

HRID 1816687 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:4][CH:3]=1.[CH3:17][C:18]([OH:22])([C:20]#[CH:21])[CH3:19].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]#[C:20][C:18]([CH3:19])([OH:22])[CH3:17])=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 22494610HCID 22494610, compound

Product 1

HCID 224946044-[4-(6-Methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of 1-bromo-4-(6-methoxyhexyloxy)benzene (3.68 g), 2-methyl-3-butyn-2-ol (1.86 ml) and triethylamine (18 ml) in pyridine (7.4 ml) was added triphenylphosphine (67.2 mg), copper(I) iodide (24.4 mg) and dichlorobis(triphenylphosphine)palladium(II) (18.0 mg), and refluxed overnight. After cooling, insoluble material was filtered off and washed with isopropyl ether. The filtrate was evaporated under reduced pressure. To the residue was added isopropyl ether and the mixture was washed with 0.1N-hydrochloric acid, water and brine. The organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude yellow oil. The crude yellow oil was purified by silica gel chromatography (10:1-2:1 hexane-ethyl acetate) to give 4-[4-(6-methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol (3.17 g) as a yellow powder.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. filtrationinsoluble material was filtered off
  4. washwashed with isopropyl ether
  5. customThe filtrate was evaporated under reduced pressure
  6. additionTo the residue was added isopropyl ether
  7. washthe mixture was washed with 0.1N-hydrochloric acid, water and brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationMagnesium sulfate was filtered off
  10. customthe filtrate was evaporated under reduced pressure
  11. customto give a crude yellow oil
  12. customThe crude yellow oil was purified by silica gel chromatography (10:1-2:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8a0ce3eecfcf4d26bbac218f7bf03c70
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884868B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes