Dichloromethane → HCID 69589285, compound

HRID 860685Notes

Reaction equation

HRID 860685 reaction equation
[C:1]([C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH:19]([CH3:21])[CH3:20])([CH3:3])=[CH2:2].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[CH3:42][O:43][C:44](=[O:55])[CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50](Br)=[CH:49][C:48]=1[CH3:54].ClCCl.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.B1C2CCCC1CCC2>O.[Cl-].[Na+].O.CN(C)C=O.O1CCCC1>[CH3:42][O:43][C:44](=[O:55])[CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:2][CH:1]([C:4]2[O:8][C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=3)=[N:6][C:5]=2[CH:19]([CH3:21])[CH3:20])[CH3:3])=[CH:49][C:48]=1[CH3:54]

Participants

10

Reactant 5

HCID 6344DichloromethaneHCID 11773TriphenylarsineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 20827035HCID 20827035, compoundHCID 69589574HCID 69589574, compound

Product 1

HCID 69589285HCID 69589285, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-Isopropenyl-4-isopropyl-2-(4-trifluoromethyl-phenyl)-oxazole (0.5 g, 1.695 mmol), 9-BBN dimer (0.46 g, 1.865 mmol), and tetrahydrofuran (5 mL) is stirred at room temperature 6 hr. The mixture is diluted with water (1 mL). In another flask, a mixture of (4-bromo-2-methyl-phenoxy)-acetic acid methyl ester (0.53 g, 2.03 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.14 g, 0.17 mmol), triphenylarsine (0.1 g, 0.339 mmol), and N,N-dimethylformamide (5 mL) is stirred in ice/water. The previously described 9-BBN solution is added via cannula and the resulting mixture is stirred at room temperature 18 hr. The black reaction mixture is diluted with water (50 mL) and brine (50 mL), and the product is extracted to ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated. The black residue is purified via silica chromatography eluting with 1:1 hexanes:dichloromethane to 1:1:0.5 hexanes:dichloromethane:ethyl acetate to afford the product as a colorless oil, 0.136 g, 17%. MS M++1 476. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. stirringthe resulting mixture is stirred at room temperature 18 hr
  2. customThe black reaction mixture
  3. extractionthe product is extracted to ethyl acetate (3×75 mL)
  4. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe black residue is purified via silica chromatography
  8. washeluting with 1:1 hexanes

Sources & evidence

ORD record
ord-3507f3548233422ab75652da331ba77b
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

Loading…