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

HRID 1669118Notes

Reaction equation

HRID 1669118 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1919c2c15f3444bc83132ae893774372
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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