Tetrahydrofuran → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate
Reaction equation
[Li].[CH3:2][C:3]([O-:6])(C)C.C[C:8]([O-:11])(C)C.CC([O-])(C)C.[Al+3].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>S(=O)(=O)(O)[O-].[Na+]>[OH:18][CH2:22][C:21]1([C:8]([O:6][CH2:3][CH3:2])=[O:11])[CH2:19][CH2:20]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91%): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).
Workup
- customThe cooled reaction mixture
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-2808f2b3e20444e1a3b7a7e8499cadcb
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422278B2
Reaction notes
Loading…