Triphenylphosphine → HCID 66681707, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:11][C@@H:12]([OH:16])[CH2:13][O:14][CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([O:16][C@@H:12]([CH3:11])[CH2:13][O:14][CH3:15])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1Participants
Procedure
3-Bromo-5-methoxyphenol (7.60 g, 37.4 mmol) synthesized in Example (1a) was dissolved in toluene (100 mL), and R-(−)-1-methoxy-2-propanol (4.40 mL, 44.9 mmol) and triphenylphosphine (13.8 g, 52.6 mmol) were added, followed by dropwise addition of diethyl azodicarboxylate (2.2 mol/l toluene solution, 24 mL, 52.8 mmol) at 0° C. and stirring at room temperature for 1.5 hours under nitrogen atmosphere. The solvent was distilled off under reduced pressure, diethyl ether (100 mL) was added, and the deposit was filtered to be removed. The mother liquor was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-20%) to afford the desired compound (9.22 g, yield 89%) as a colorless liquid.
Workup
- distillationThe solvent was distilled off under reduced pressure, diethyl ether (100 mL)
- additionwas added
- filtrationthe deposit was filtered
- customto be removed
- distillationThe mother liquor was distilled off under reduced pressure
- customthe resulting residue was purified
- washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-20%)
Sources & evidence
- ORD record
- ord-9312f7db2ce54388aeec08ffd6feadc0
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017610B2
Reaction notes
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