Triphenylphosphine → HCID 21263166, compound

HRID 567883Notes

Reaction equation

Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[C:14](OC)[CH:13]=[C:12]([O:18]C)[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:23]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(OCC)(=O)C.[Cu](I)I>[CH2:22]([C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:18])[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one 500 mg (F. W. 349.18, 1.43 mmol) prepared in the first stage of Production Example 79, triphenylphosphine 75 mg (F. W. 262.29, 0.062 mmol), trisbenzyldene acetone dipalladium chloroform complex 74 mg (F. W. 1035.08, 0.015 mmol), diisopropylethylamine 575 μl (F. W. 98.22, d=0.742, 2.86 mmol), ethynyl trimethylsillane 350 μl (F. W. 98.22, d=0.742, 2.86 mmol) and copper iodide 27.5 mg (F. W. 190.44, 0.143 mmol) were dissolved in N-methyl-2-pyrrolidone (5 ml) and, after substituting with argon atmosphere, they were stirred with heating at 80° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography to give the title compound 420 mg (F. W. 367.419, 66%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

Workup

washwashed with water and saturated sodium chloride solution
customThe organic layer was dried
concentrationconcentrated
customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-6d299c3be5b34cc293512871c358c2e4
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180659B2

Reaction notes

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