4-Fluorophenol → HCID 13831434, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:14][CH2:15][CH3:16])(=[O:13])[C@H:10]([CH3:12])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:15]([O:14][C:9](=[O:13])[C@H:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:12])[CH3:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
Under argon, 100 g (0.892 mol) of 4-fluorophenol (2) was combined with 105.2 g (0.892 mol) of (S)-ethyl lactate and 233.8 g (0.892 mol) of triphenylphosphine in 1200 mL of tetrahydrofuran (THF). The reaction mixture was cooled to −5° C., and 180.4 g (0.892 mol) of diisopropylazodicarboxylate (DIAD) in 500 ml of THF was dropwise added. The ice bath was removed, and stirring was continued at room temperature for 18-22 hr. THF was then evaporated in vacuo, and 1400 mL of hexane-ether (80:20) was added to the residue, and the remaining solid was removed by filtration. The filtrate was then washed with 2×600 mL of 1N NaOH, followed by 2×600 mL of water and 600 mL of brine. The washed filtrate was then dried over MgSO4, filtered and then evaporated to give 185 g of (R)-ethyl-2-(4-fluorophenoxy)-propionate, 7, as a light yellow oil in 98% yield, Bp 80° C. at 0.7 mm Hg. The reaction is shown as follows:
Workup
- customThe ice bath was removed
- customTHF was then evaporated in vacuo, and 1400 mL of hexane-ether (80:20)
- additionwas added to the residue
- customthe remaining solid was removed by filtration
- washThe filtrate was then washed with 2×600 mL of 1N NaOH
- dry with materialThe washed filtrate was then dried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-86db97dd1b48418d9a849d1da9a1059f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158667B2
Reaction notes
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