Sodium Carbonate → 5-(2,2,2-Trifluoro-1,1-dimethyl-ethoxy)-pyridine-2-carbonitrile

HRID 911304

反応式

HRID 911304 の反応式
[F:1][C:2]([F:8])([F:7])[C:3]([OH:6])([CH3:5])[CH3:4].[H-].[Na+].F[C:12]1[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(P(N(C)C)(N(C)C)=O)C>[F:1][C:2]([F:8])([F:7])[C:3]([CH3:5])([CH3:4])[O:6][C:12]1[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 113324532-Cyano-5-fluoropyridine

生成物 1

HCID 576566265-(2,2,2-Trifluoro-1,1-dimethyl-ethoxy)-pyridine-2-carbonitrile収率 79.4%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

Add 2-trifluoromethyl-2-propanol (1.1 g, 8.3 mmol) slowly to a slurry of sodium hydride (202 mg, 60% mineral oil, washed with hexane) in HMPA (3 mL) under nitrogen. Stir the slurry for 15 min, then add 5-fluoro-pyridine-2-carbonitrile (510 mg, 4.2 mmol). Stir the slurry for 16 h at ambient temperature. Adjust the mixture to pH 9 with sodium carbonate then extract with diethyl ether (3×50 mL). Collect the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (95/5 to 80/20) to obtain the desired intermediate (768 mg, 79%). GC-MS m/z: 230 (Me).

後処理

  1. stirringStir the slurry for 16 h at ambient temperature
  2. extractionthen extract with diethyl ether (3×50 mL)
  3. customCollect the organic layer
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (95/5 to 80/20)

出典と根拠

ORDレコード
ord-a77b1277e1ac4efd8e56ec36ce2c3f17
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

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