Hydrochloric Acid → Benzyl-N,N-dimethylglycolamide

HRID 479759ノート

反応式

HRID 479759 の反応式
[Cl-].[CH3:2][N:3]([Al+]C)[CH3:4].[CH2:7]([CH:14]([OH:19])[C:15](OC)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1(C)C=CC=CC=1>[CH2:7]([CH:14]([OH:19])[C:15]([N:3]([CH3:4])[CH3:2])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 518800Methyl 2-hydroxy-3-phenylpropanoateHCID 86751577Dimethylamino(methyl)aluminum chloride

生成物 1

HCID 18771503Benzyl-N,N-dimethylglycolamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To dimethylamino(methyl)aluminum chloride [prepared from dimethylamine hydrochloride (3.4 g, 42 mmoL) and trimethyl aluminum (21 mL of 2 M solution, 42 mmol)] in toluene (40 mL) was added methyl benzylglycolate (3.0 g, 17 mmol). After stirring at rt for 1.5 h, the mixture was poured into 3 N HCl and extracted with Et2O. The organic extract was washed with saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 9-50% EtOAc/Hex. The title compound was obtained as a colorless oil (1.2 g, 37%): 1H NMR CDCl3): d 7.4-7.1 (m, 5H); 4.61 (s, 2H); 4.18 (s, 2H); 2.98 (s, 3H); 2.95 (s, 3H).

後処理

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with a solvent gradient of 9-50% EtOAc/Hex

出典と根拠

ORDレコード
ord-fb91c31132804665a9b5e5da5a3d2605
出典データセット
uspto-grants-2003_11
特許番号
US06645989B2

反応ノート

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