Sodium Carbonate → HCID 178421998, Verbindung

HRID 572489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572489
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Br)=[C:14]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[O:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:38]2[C:39]([CH3:48])=[C:40]3[C:45](=[CH:46][CH:47]=2)[O:44][CH2:43][CH2:42][CH2:41]3)O1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:38]3[C:39]([CH3:48])=[C:40]4[C:45](=[CH:46][CH:47]=3)[O:44][CH2:43][CH2:42][CH2:41]4)=[C:14]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[O:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 574162234,4,5,5-Tetramethyl-2-(5-methylchroman-6-yl)-1,3,2-dioxaborolaneHCID 1317328254-Bromo-3-(2-tert-butylsilyloxypropan-2-yl)-7-phenylmethoxyisochromen-1-one

Produkt 1

HCID 178421998HCID 178421998, VerbindungAusbeute 14,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 7-Benzyloxy-4-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-isochromen-1-one (30 g, 63.1 mmol) and 4,4,5,5-tetramethyl-2-(5-methylchroman-6-yl)-1,3,2-dioxaborolane (51.9 g, 89 mmol) in 1,4-dioxane/H2O (400/100 mL) was added Pd(dppf)Cl2 (4.62 g, 6.31 mmol), Na2CO3 (20 g, 189 mmol), and PPh3 (4.96 g, 18.93 mmol). The resultant mixture was stirred at refluxing under N2. After 12 h, the reaction mixture was cooled to ambient temperature and partitioned between dichloromethane and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography column on silica gel to afford title product as a pale solid (5.0 g). LCMS (10-80 AB—2MIN.M): Rt=1.541, purity=93.3%, M+1=542.

Aufarbeitung

  1. temperatureat refluxing under N2
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography column on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-795f411b8cb642719488469ff3634dfa
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029391B2

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