Ethanol → ethyl 2,3-dihydro-1H-indene-2-carboxylate
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].OS(O)(=O)=O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:11][C:10]([CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:12])[CH3:19]Participants
Conditions
- Temperature
- 75 °C
Procedure
To a solution of indan-2-carboxylic acid (2.50 g) in ethanol (77 mL) at 25° C. was added concentrated H2SO4 (9 mL). The colorless solution was stirred at 75° C. over a period of 48 h. Solvent was removed under reduced pressure and the residue was diluted with dichloromethane (10 mL) and water (10 mL). The pH of the solution was brought from 1 to 14. Two layers were separated and the aqueous phase was extracted with ethyl acetate (30 mL). Organic layers were combined, dried over magnesium sulfate, filtered and concentrated under high vacuum. The solid obtained was purified on a Biotage™ 40M column (silica, hexanes/ethyl acetate 1:0 to 97:3) to give indan-2-carboxylic acid ethyl ester. Off-white oil; 1H NMR (400 MHz, CDCl3): δ 7.22-7.14 (m, 4H), 4.19 (q, J=7.04 Hz, 4H), 3.36-3.10 (m, 5H), 1.29 (t, J=7.04 Hz, 3H); LRMS (ESI): m/z 190 (MH+); HPLC: 4.3 min.
Workup
- customSolvent was removed under reduced pressure
- additionthe residue was diluted with dichloromethane (10 mL) and water (10 mL)
- customTwo layers were separated
- extractionthe aqueous phase was extracted with ethyl acetate (30 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under high vacuum
- customThe solid obtained
- customwas purified on a Biotage™ 40M column (silica, hexanes/ethyl acetate 1:0 to 97:3)
Sources & evidence
- ORD record
- ord-59c67551baf941e9b27c7b3227419a71
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927765B2
Reaction notes
Loading…