Sodium Carbonate → HCID 178421998、化合物

HRID 572489ノート

反応式

HRID 572489 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 178421998HCID 178421998、化合物収率 14.6%

試薬・触媒・溶媒 2

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-795f411b8cb642719488469ff3634dfa
出典データセット
uspto-grants-2015_05
特許番号
US09029391B2

反応ノート

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