Hydrochloric Acid → Benzyl-N,N-dimethylglycolamide

HRID 2293495노트

반응식

HRID 2293495 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 2M 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 3N 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): δ7.4-7.1 (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-c5bf19594412486cbfbf19f8bddad4dd
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686455

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