Sodium Carbonate → HCID 22274583、化合物

HRID 494853

反応式

HRID 494853 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH3:16].[I:17]N1C(=O)CCC1=O.CN(C)C(=N)N(C)C.[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+].P([O-])(O)(O)=O.[K+]>CCOCC.CN(C=O)C>[OH:1][C:2]1[C:7]([I:17])=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH3:16]

参加物

9

反応物 6

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 664601,1,3,3-TetramethylguanidineHCID 120273N-IodosuccinimideHCID 516951Monobasic potassium phosphateHCID 222744974'-Hydroxy-3'-methyl-[1,1'-biphenyl]-4-carbonitrile

生成物 1

HCID 22274583HCID 22274583、化合物収率 17%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

4′-hydroxy-3′-methyl-1,1′-biphenyl-4-carbonitrile (875 mg, 4.18 mmol) was dissolved into DMF (20 mL) and treated with N-iodosuccinimide (1.012 g, 4.5 mmol). The solution was stirred at room temperature for four days. Then the mixture was stirred with tetramethylguanidine (1 mL) for ten minutes, poured into an aqueous mixture of Na2SO3 and Na2CO3, adjusted to pH 9 with aqueous potassium dihydrogen phosphate, and diluted with ether. The gum which separated from the biphasic mixture was dissolved into EtOAc and added to a rapidly stirred mixture of the aqueous phase and ether. The organic phase was separated, filtered, combined with the original ethereal phase, concentrated, and chromatographed through silica with a 50% to 100% gradient of CH2Cl2/hexanes to provide the title compound as an off-white powder (17% yield). MS (ESI APCI negative ion detection) m/z 334 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 7.26 (s, 1H), 7.33 (d, 1H), 7.60 (d, 2H), 7.66-7.74 (m, 3H).

後処理

  1. customThe gum which separated from the biphasic mixture
  2. dissolutionwas dissolved into EtOAc
  3. additionadded to a rapidly stirred mixture of the aqueous phase and ether
  4. customThe organic phase was separated
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed through silica with a 50% to 100% gradient of CH2Cl2/hexanes

出典と根拠

ORDレコード
ord-1cbe502cab4a40aaa92da89356bd699c
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

関連ノート

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