Hydrochloric Acid → Benzyl-N,N-dimethylglycolamide

HRID 479759노트

반응식

HRID 479759 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 18771503Benzyl-N,N-dimethylglycolamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fb91c31132804665a9b5e5da5a3d2605
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645989B2

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