Cornforth reagent → Methyl 2-hydroxy-4-[3-oxo-3-(4,4-dimethylthiochroman-6-yl)-1-propynyl]benzoate
Reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]([OH:27])[C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[S:21][CH2:20][CH2:19][C:18]3([CH3:26])[CH3:25])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14](=[O:27])[C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[S:21][CH2:20][CH2:19][C:18]3([CH3:25])[CH3:26])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Participants
4
Procedure
2 g (5.2 mmol) of methyl 2-hydroxy-4-[3-hydroxy-3-(4,4-dimethylthiochroman-6-yl)-1-propynyl]benzoate and 50 ml of dichloromethane were introduced into a round-bottomed flask. 2.6 g (6.9 mmol) of pyridinium dichromate were added and stirring was carried out at room temperature for 8 hours. The reaction mixture was evaporated to dryness and the residue obtained purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (50/50). After evaporating the solvents, 1.3 g (65%) of the expected ester was recovered in the form of a brown oil.
Workup
- customThe reaction mixture was evaporated to dryness
- customthe residue obtained
- custompurified by chromatography on a silica column
- washeluted with a mixture of dichloromethane and hexane (50/50)
- customAfter evaporating the solvents, 1.3 g (65%) of the expected ester
- customwas recovered in the form of a brown oil
Sources & evidence
- ORD record
- ord-212ebbff58c245ce88a151998225a5d2
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716624
Reaction notes
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