Acetic Acid → HCID 5127212、化合物

HRID 2208832ノート

反応式

HRID 2208832 の反応式
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.O>[CH2:14]([NH:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 4313471Ethyl 3-Amino-2-methylbenzoateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 5127212HCID 5127212、化合物収率 101.1%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

実験手順

To a stirred solution of ethyl 3-amino-2-methylbenzoate (1.00 g, 5.58 mmol) in DCE (20 ml) was added benzaldehyde (569 μl, 5.58 mmol) followed by acetic acid (0.64 ml, 11.2 mmol). The reaction was stirred at room temperature for 1 h and then sodium triacetoxyborohydride (1.77 g, 8.37 mmol) was added and the reaction stirred for 2 h. Distilled water (20 ml) was added and solid NaHCO3 was added until the aqueous phase was pH7 and the phases were separated. The aqueous phase was washed with DCM (2×5 0 ml), the combined organics were then washed with brine (50 ml), dried using Na2SO4, filtered and evaporated to afford the title compound as a yellow oil (1.52 g, 96%) which was used in the next stage without any further purification. LC-MS 95%, m/z=270.0, 1H NMR (500 MHz, Chloroform-d) δ 7.42-7.32 (m, 4H), 7.32-7.28 (m, 1H), 7.17-7.06 (m, 2H), 6.73 (dd, J=7.8, 1.1 Hz, 1H), 4.40 (s, 2H), 4.36 (q, J=14.3, 5.3 Hz, 2H), 4.08 (br. s, 1H), 2.35, (s, 3H), 1.39 (t, 3H).

後処理

  1. stirringthe reaction stirred for 2 h
  2. customthe phases were separated
  3. washThe aqueous phase was washed with DCM (2×5 0 ml)
  4. washthe combined organics were then washed with brine (50 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-7267f3a5528f4070a239597283d86101
出典データセット
uspto-grants-2016_06
特許番号
US09376422B2

反応ノート

読み込み中…