Triphenylphosphine → 3-(2,6-Dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine

HRID 1627512ノート

反応式

HRID 1627512 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[C:35]([Cl:40])[C:34]=1[CH:41]([OH:43])C.O[C:45]1[C:46]([N+:51]([O-:53])=[O:52])=[N:47][CH:48]=[CH:49][CH:50]=1>C1(C)C=CC=CC=1.C1COCC1>[Cl:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[C:35]([Cl:40])[C:34]=1[CH2:41][O:43][C:45]1[C:46]([N+:51]([O-:53])=[O:52])=[N:47][CH:48]=[CH:49][CH:50]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 270573-Hydroxy-2-nitropyridineHCID 5462977Diethyl azodicarboxylateHCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

生成物 1

HCID 211113993-(2,6-Dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine収率 100%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of triphenyl phosphine (8.2 g, 0.03 mol) and DEAD (13.65 mL of a 40% solution in toluene) in THF (200 mL) at 0° C. was added a solution of 1-(2,6-dichloro-3-fluoro-phenyl)ethanol (4.55 g, 0.021 mol) and 3-hydroxy-nitropyridine (3.35 g, 0.023 mol) in THF (200 mL). The resulting bright orange solution was stirred under a nitrogen atmosphere at ambient temperature for 4 hours at which point all starting materials had been consumed. The solvent was removed, and the crude material was dry loaded onto silica gel, and eluted with ethyl acetate-hexanes (20:80) to yield 3-(2,6-dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine (6.21 g, 0.021 mol, 98%) as a pink solid. 1H NMR (CDCl3, 300 MHz) δ1.8-1.85 (d, 3H), 6.0-6.15 (q, 1H), 7.0-7.1 (t, 1H), 7.2-7.21 (d, 1H), 7.25-7.5 (m, 2H), 8.0-8.05 (d, 1H).

後処理

  1. customhad been consumed
  2. customThe solvent was removed
  3. dry with materialthe crude material was dry
  4. washeluted with ethyl acetate-hexanes (20:80)

出典と根拠

ORDレコード
ord-75bc75fb3d9f42d6b1e7a67c5e8625d3
出典データセット
uspto-grants-2014_07
特許番号
US08785632B2

反応ノート

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