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

HRID 1669118

反応式

HRID 1669118 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1919c2c15f3444bc83132ae893774372
出典データセット
uspto-grants-2011_08
特許番号
US07989451B2

関連ノート

読み込み中…