2-Methyl-3-butyn-2-ol → HCID 66582304, compound

HRID 1972364Notes

Reaction equation

HRID 1972364 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].[CH3:30][C:31]([OH:35])([C:33]#[CH:34])[CH3:32].C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(N(C)C)=O>[CH3:30][C:31]([OH:35])([C:33]#[C:34][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9])[CH3:32]

Participants

7

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 56932983HCID 56932983, compound

Product 1

HCID 66582304HCID 66582304, compoundYield 10.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A 20 mL vial was charged with 2-(3′-chloro-4′-(phenylsulfonyl)-4-biphenylyl)-1,1,1-trifluoro-2-propanol (0.300 g, 0.680 mmol, Example 19), 2-methyl-3-butyn-2-ol (0.099 mL, 1.021 mmol, Sigma-Aldrich, St. Louis, Mo.), potassium carbonate (0.235 g, 1.701 mmol), 2 mL of dimethylacetamide, 2-(dicyclohexylphosphino)-2′,4′,6′,-triisopropyl-biphenyl (XPhos) (9.73 mg, 0.020 mmol, Strem Chemical Inc, Newburyport, Mass.), and tris(dibenzylideneacetone)dipalladium (0) (0.021 g, 0.020 mmol, Strem Chemical Inc, Newburyport, Mass.). The vial was sealed and heated at 100° C. for 2 h. After that time, the mixture was concentrated and purified by column chromatography (40 g of silica, 0 to 40% EtOAc in hexane) to give 2-methyl-4-(4-(phenylsulfonyl)-4′-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-3-biphenylyl)-3-butyn-2-ol (0.035 g) as a mixture of two enantiomers.

Workup

  1. customThe vial was sealed
  2. concentrationAfter that time, the mixture was concentrated
  3. custompurified by column chromatography (40 g of silica, 0 to 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-c4ae214f7dec4ee79eff8fb97a754976
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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