Hydrochloric Acid → HCID 19382375, compound
Reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.C([N-]C(C)C)(C)C.[Li+].C1COCC1.C(C1C=CC=CC=1)C.CCCCCCC.CON(C)[C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].Cl>O1CCCC1>[C:40]([C:2]1[O:1][CH:5]=[CH:4][C:3]=1[C:6]([OH:8])=[O:7])(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of 3-furoic acid (8.97 g, 0.08 mol) in tetrahydrofuran (200 ml) was cooled to -70° C. and a 2.0M solution of lithium diisopropylamide in THF-ethylbenzene-heptane (80 ml, 0.16 mol) was added dropwise over 3/4 hr at -70° to -20° C. under nitrogen to give a tan suspension. A red solution formed after stirring for 113/4 hours at -20° C. To this solution was added N-methoxy-N-methylpivalamide (11.67 g, 0.08 mol) in tetrahydrofuran (10 ml) at -40° C. The reaction mixture was left at ambient temperature overnight. Then ,it was cooled in ice and neutralized with 6N ethanolic hydrogen chloride (50 ml). The neutralized solution was acidified with 1.5N HCl (150 ml) and was extracted with ether (300 ml). The ether extracts were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated in vacuo to a brown solid (15.4 g). Chromatography on silica gel using hexane-THF-acetic acid (10-2-0.2) gave a yellow solid (9.8 g), mp 85°-89° C.
Workup
- customto give a tan suspension
- customA red solution formed
- waitThe reaction mixture was left at ambient temperature overnight
- extractionwas extracted with ether (300 ml)
- washThe ether extracts were washed with saturated NaCl
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo to a brown solid (15.4 g)
Sources & evidence
- ORD record
- ord-f60236869e37428fb6d6cd8b4467a2da
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05453424
Reaction notes
Loading…