Triethylamine → Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoate

HRID 2037353ノート

反応式

HRID 2037353 の反応式
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=O)[NH2:17])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([C:16]#[N:17])=[CH:13][C:14]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

生成物 1

HCID 66935544Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoate収率 64.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice-cooled solution of 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.00 g, 25.2 mmol) and triethylamine (7.66 g, 75.7 mmol) in DCM (100 mL), trifluoroacetic anhydride (6.06 g, 28.8 mmol) is added slowly so that the reaction temperature stays below 15° C. The clear yellow solution is stirred at rt for 1 h before it is washed twice with water (100 mL) and concentrated. The crude product is purified by recrystallisation from methanol to give 3-(4-cyano-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (4.2 g) as a white solid, 1H NMR (CDCl3): δ 1.48 (s, 9H), 2.33-2.37 (m, 2H), 2.38 (s, 6H), 2.94-3.01 (m, 2H), 7.31 (s, 2H).

後処理

  1. additionis added slowly so that the reaction temperature
  2. customstays below 15° C
  3. washis washed twice with water (100 mL)
  4. concentrationconcentrated
  5. customThe crude product is purified by recrystallisation from methanol

出典と根拠

ORDレコード
ord-d8d1536fbfca487f8f4f724d2bf0dac6
出典データセット
uspto-grants-2013_11
特許番号
US08575200B2

反応ノート

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