Methanol → HCID 11391236、化合物

HRID 1685326ノート

反応式

HRID 1685326 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][CH:4]=1.[Li][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.CO.[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][N+:11]([O-:13])=[O:12])=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 697963trans-4-Methoxy-beta-nitrostyreneHCID 178506676HCID 178506676、化合物

生成物 1

HCID 11391236HCID 11391236、化合物収率 68%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a cold (−78° C.), stirred solution of (E)-1-methoxy-4-(2-nitrovinyl)benzene (153 mg, 0.86 mmol) in THF (20 mL) was added PhLi (0.64 mL, 1.6M) under Ar. After 1.5 h, the reaction was treated with MeOH, sat. NH4Cl and brine, and allowed to warm to room temperature. The reaction was extracted with EtOAc (3×), dried (MgSO4), filtered, concentrated then purified on Biotage Horizon to provide the product (150 mg, 68%) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm: 7.32 (2H, t, J=7.20 Hz), 7.19-7.25 (3H, m), 7.14 (2H, d, J=8.84 Hz), 6.84 (2H, d, J=8.84 Hz), 4.90-4.96 (2H, m), 4.81-4.87 (1H, m), 3.77 (3H, s).

後処理

  1. extractionThe reaction was extracted with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthen purified on Biotage Horizon

出典と根拠

ORDレコード
ord-5c3a25fb906b48208da953184c5cbc35
出典データセット
uspto-grants-2012_04
特許番号
US08148400B2

反応ノート

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