Triphenylphosphine → Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate

HRID 2368874ノート

反応式

HRID 2368874 の反応式
[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH2:14]O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Cl:43])C(=O)C1>C(Cl)Cl>[Cl:43][CH2:14][C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([N:2]([CH3:16])[CH3:1])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 68335184Ethyl 3-(dimethylamino)-5-(hydroxymethyl)benzoate

生成物 1

HCID 68335175Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Compound 2 (3.45 g, 15.452 mmol) and PPh3 (6.14 g, 23.17 mmol) in 70 mL of DCM was added NCS (3.19 g, 23.178 mmol) at 0° C. The reaction mixture was stirred for 1.5 hours. After removal of solvent under reduced pressure, the residue was dissolved in Et2O. The solution was washed with brine and dried with MgSO4. The solution was filtered and concentrated. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=9.5/0.5) to give Compound 3 (3.585 g, 96%). 1H-NMR (500 MHz, CDCl3) δ 7.38 (s, 1H), 7.35 (s, 1H), 6.89 (s, 1H), 4.57 (s, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.00 (s, 6H), 1.39 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, CDCl3) δ 166.73, 150.63, 138.35, 131.59, 117.31, 116.20, 113.22, 60.95, 46.40, 40.43, 14.31; ESI-MS: m/z (MH+): 242.0942 (calc'd), 242.0944 (found).

後処理

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in Et2O
  3. washThe solution was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-64a0cd2b68f24191bab7483321b13776
出典データセット
uspto-grants-2014_04
特許番号
US08703815B2

反応ノート

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