4-Methoxyphenol → HCID 131728730, compound
Reaction equation
[C:1]([C:4]([C@@:6]([C:21](=[O:23])[CH3:22])([C@@:8]([C:18](=[O:20])[CH3:19])([C@:10]([C:15](=[O:17])[CH3:16])([C@H:12]([CH3:14])[OH:13])[OH:11])[OH:9])[OH:7])=[O:5])(=[O:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1>ClCCl>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C@@:15]2([CH3:16])[O:17][C@@:4]([C:1](=[O:3])[CH3:2])([OH:5])[C@:6]([C:21](=[O:23])[CH3:22])([OH:7])[C@:8]([C:18](=[O:20])[CH3:19])([OH:9])[C@@:10]2([C:12](=[O:13])[CH3:14])[OH:11])=[CH:28][CH:27]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1,2,3,4-Tetraacetyl-L-rhamnose (19.2 g, 57.8 mmol) and p-methoxyphenol (MPOH) (12.2 g, 98.3 mmol) were dissolved in 150 mL of dichloromethane and cooled to 0° C. BF3 OEt2 (23.0 g, 20.5 mL, 162.0 mmol) was added and the mixture stirred overnight while warming to room temperature. The reaction mixture was quenched by addition of saturated NaHCO3 solution, washed 2 times with water, dried over Na2SO4, concentrated and the residue was purified by column chromatography (3:1 hexane/EtOAc) yielding 18.3 g (80%) of 4-methoxyphenyl 1,2,3,4-tetraacetyl-α-L-rhamnose. 4-Methoxyphenyl 1,2,3,4-tetraacetyl-α-L-rhamnose (18.0 g, 45.4 mmol) was dissolved in 300 mL of methanol and 9 mL of 0.5 M NaOMe solution were added. The mixture was stirred for 12 h, the solvent was removed in vacuo. Column chromatography (4:1 dichloromethane/methanol) afforded 2.63 g (96%) as a colorless solid.
Workup
- temperaturewhile warming to room temperature
- customThe reaction mixture was quenched by addition of saturated NaHCO3 solution
- washwashed 2 times with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customthe residue was purified by column chromatography (3:1 hexane/EtOAc)
Sources & evidence
- ORD record
- ord-b1add73afe984d4c89ea74820e271f88
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07901687B2
Reaction notes
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