Methanol → HCID 11391236, 화합물

HRID 1685326노트

반응식

HRID 1685326 반응식
[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

참가 물질

7

반응물 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 697963trans-4-Methoxy-beta-nitrostyreneHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 11391236HCID 11391236, 화합물수율 68%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5c3a25fb906b48208da953184c5cbc35
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148400B2

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