Ethanol → Ethyl 2-(2,3-dihydro-1H-inden-2-yl)acetate

HRID 1669118

반응식

HRID 1669118 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([OH:13])=[O:12].[CH3:14][CH2:15]O>>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

3

반응물 2

HCID 702EthanolHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

생성물 1

HCID 10104359Ethyl 2-(2,3-dihydro-1H-inden-2-yl)acetate수율 90%

실험 절차

A solution of acid 147 (32.0 g, 180 mmol) in dry EtOH (250 mL) and CH2SO4 (2.0 mL) was stirred at reflux temperature under N2 for 16 h. The solvent was evaporated, the residue partitioned between ice/water (200 mL) and DCM (50 mL) and the aqueous layer extracted with DCM (2×40 mL). The combined organic layer was washed with saturated aqueous NaHCO3 solution and water, dried and the solvent evaporated to yield ester 148 (33.3 g, 90%) (lit. Tanaka, et. al., J. Med. Chem. 1994, 37, 2071-2078) as a brown oil: 1H NMR δ 7.10-7.21 (m, 4H, H-4, H-5, H-6, H-7), 4.15 (q, J=7.1 Hz, 2H, CH2), 3.10-3.45 (m, 2H, H-1, H-3), 2.82-2.94 (m, 1H, H-2), 2.62-2.68 (m, 2H, H-1, H-3), 4.48 (d, J=7.4 Hz, 2H, CH2CO2), 1.27 (t, J=7.1 Hz, 2H, CH3).

후처리

  1. temperatureat reflux temperature under N2 for 16 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ice/water (200 mL) and DCM (50 mL)
  4. extractionthe aqueous layer extracted with DCM (2×40 mL)
  5. washThe combined organic layer was washed with saturated aqueous NaHCO3 solution and water
  6. customdried
  7. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-1919c2c15f3444bc83132ae893774372
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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