Acetic Acid → HCID 13576467、化合物

HRID 225903

反応式

HRID 225903 の反応式
CN.CO.[S:5]1[CH:9]=[C:8]([CH:10]=O)[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]1=2.CC(O)=O.[BH3-][C:21]#[N:22].[Na+]>>[CH3:21][NH:22][CH2:10][C:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[S:5][CH:9]=1

参加物

6

反応物 5

HCID 176Acetic AcidHCID 887MethanolHCID 6329MethylamineHCID 2273281-Benzothiophene-3-carbaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 13576467HCID 13576467、化合物収率 48%

実験手順

To a stirred solution of 2 M methylamine in methanol (75 mmole, 150 mmole) was added benzo[b]thiophen-3-carboxaldehyde (5.3 g, 33 mmole) and HOAc (43 mL, 75 mmole). The reaction was stirred at RT for 1 h, then NaBH3CN (2.1 g, 33 mmole) was added portionwise over 5 minutes. The reaction was stirred for an additional 16 b then was concentrated under vacuum. The residue was taken up in Et2O (300 mL) and washed with 1.0 N NaOH (300 mL) then with brine, dried (Na2SO4), and concentrated. Purification by flash chromatography on silica gel (5% (5% NH4OH/MeOH)/CHCl3) gave the title compound (2.81 g, 48%) as a brownish oil: 1H NMR (400 MHz, CDCl3) δ•7.87 (2d, 2 H), 7.40 (m, 2 H), 7.32 (s, 1 H), 4.02 (s, 2 H), 2.56 (s, 3 H), 1.5 (br s, 1 H).

後処理

  1. stirringThe reaction was stirred for an additional 16 b
  2. concentrationthen was concentrated under vacuum
  3. washwashed with 1.0 N NaOH (300 mL)
  4. dry with materialwith brine, dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (5% (5% NH4OH/MeOH)/CHCl3)

出典と根拠

ORDレコード
ord-c9d59e2993104c6f9f2a46ea2a895260
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

関連ノート

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