Propargyl alcohol → HCID 18176104, compound
Reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]>>[CH2:3]([O:6][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:4]#[CH:5]Participants
Conditions
- Temperature
- 25 °C
Procedure
Sodium hydride (420 mg, 8.75 mmol) was added to propargyl alcohol (68 mL, 1.17 mol) at 4° C. and stirred for 30 minutes at 25° C. 10-Bromodecanoic acid (2g, 7.96 mmol) was added to this mixture and the reaction was stirred at 98° C. for 48 hrs. The reaction mixture was extracted with water and ethyl acetate at pH 1. After drying the organic phase over sodium sulfate, the solvent was removed at reduced pressure. Product was purified over silica gel chromatography in 7-10% ethyl acetate/hexane/0.3% formic acid and then over a second silica gel column in 1-2.5% ethyl acetate/benzene/0.3% formic acid to yield 10-(2-propynoxy)decanoic acid (245 mg, 14%). mp <30° C.; 1H NMR (300 MHz, CDC13) δ 1.25-1.42 (br, 10H, methylene envelope), 1.54-1.70 (bm, 4H, OCH2CH2, CH2CH2COOH), 2.35 (t, 2H, J=7.4, CH2COOH), 2.43 (t, 1H, J=2.3, HC=C), 3.52 (t, 2H, J=6.8, OCH2), 4.14 (d, 2H, J=2.5, C=CCH2O), 10.42 (br, 1H, COOH); 13C NMR (75.4 MHz, CDC13) δ 24.68, 26.06, 29.04, 29.17, 29.35*, 29.46, 34.09, 57.95, 70.22, 74.09, 79.90, 180.02; m/z 227 (M+H).
Workup
- stirringthe reaction was stirred at 98° C. for 48 hrs
- extractionThe reaction mixture was extracted with water and ethyl acetate at pH 1
- dry with materialAfter drying the organic phase over sodium sulfate
- customthe solvent was removed at reduced pressure
- customProduct was purified over silica gel chromatography in 7-10% ethyl acetate/hexane/0.3% formic acid
Sources & evidence
- ORD record
- ord-4ab701fd254242508c70b073a1c80178
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05073571
Reaction notes
Loading…