2-Methyl-3-butyn-2-ol → HCID 59558341, compound

HRID 1175142Notes

Reaction equation

HRID 1175142 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].Br[C:8]1[CH:13]=[CH:12][C:11]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C>CN(C=O)C.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>[CH3:1][C:2]([OH:6])([C:4]#[C:5][C:8]1[CH:13]=[CH:12][C:11]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)=[CH:10][CH:9]=1)[CH3:3]

Participants

6

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 107553762-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 59558341HCID 59558341, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Methyl-but-3-yn-2-ol (24 ml; 247 mmol), 2-(4-bromo-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (8.7 g; 30.85 mmol) (J.Organomet. Chem. 2006, 691(26), 5725), Pd(PPh3)2Cl2 (4.33 g; 6.17 mol) Cul (1.17 g; 6.17 mmol) in DMF (140 ml) and triethylamine (60 ml) are heated to 110° C. for 20 minutes. The reaction mixture is evaporated to dryness and the residue taken up in hexanes/acetone (85:15), filtered and the filtrate purified via chromatography ((SiO2; hexaneslacetone 85:15) to deliver the target compound as light-brown crystals. 1H-NMR (400 MHz; DMSO-d6): 7.65 (d, 2H); 7.40 (d, 2H); 5.51 (s, 1H); 1.48 (s, 6H); 1.31 (s, 12H). MS (m/z) ES+: 269 (100).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. filtrationfiltered
  3. customthe filtrate purified via chromatography ((SiO2; hexaneslacetone 85:15)

Sources & evidence

ORD record
ord-5fbf2ece550c42358069457d3ce2b487
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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