Toluene → Methyl (2s)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate

HRID 2113156노트

반응식

HRID 2113156 반응식
F[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C@@:5]([OH:11])([CH2:9][CH3:10])[C:6]([OH:8])=[O:7].[CH3:16]N(C=O)C.C1(C)C=CC=CC=1.[H-].[Na+]>O>[CH2:9]([C@@:5]1([C:6]([O:8][CH3:16])=[O:7])[CH2:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[O:11]1)[CH3:10]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11171855(2S)-2-(2-Fluoro-benzyl)-2-hydroxy-butyric acid

생성물 1

HCID 57358441Methyl (2s)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

To a solution of the acid from step 1 (4.0 g, ca. 20 mmol) in 1:4 DMF:toluene (100 mL.) was added 60% NaH in mineral oil (1.76 g, 44 mmol) in 3 portions. The reaction mixture was stirred at 110° C. under N2 for 4 hrs. The reaction was cooled to room temperature and poured into cold water (100 mL). The aqueous layer was washed with hexane (50 mL), acidified with 2 N aqueous HCl and extracted with ethyl acetate (3×50 mL). The extracts were washed with brine (50 mL), dried and concentrated. The residue was dissolved in 7:1 benzene:MeOH (80 mL) and treated with TMSCHN2 (1M in hexane) until gas evolution ceased. The reaction was concentrated and the residue was chromatographed on silica gel eluting with 85:15 hexane:ethylacetate to give methyl (2S)-2-ethyl-2,3-dihydro-benzofuran-2-carboxylate.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washThe aqueous layer was washed with hexane (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe extracts were washed with brine (50 mL)
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 7:1 benzene
  8. additionMeOH (80 mL) and treated with TMSCHN2 (1M in hexane) until gas evolution
  9. concentrationThe reaction was concentrated
  10. customthe residue was chromatographed on silica gel eluting with 85:15 hexane

출처 및 근거

ORD 기록
ord-f792c5cd496448999b4a07e13277c14c
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524882B2

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