2-Bromo-6-methoxynaphthalene → HCID 19763897, compound
Reaction equation
[Mg].Br[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.[CH3:15][Si:16]([CH3:24])([CH3:23])[O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20]>>[CH3:14][O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([C:19](=[O:20])[CH:18]([O:17][Si:16]([CH3:24])([CH3:23])[CH3:15])[CH3:22])[CH:12]=[CH:11]2Participants
Procedure
When Z is a group which is convertible to a suitable leaving group, the conversion of Z can take place either before step A or thereafter, but before step B. For example, when the magnesium Grignard of 2-bromo-6-methoxynaphthalene is contacted with (S) 2-trimethylsiloxypropionyl chloride, (S) 1-(6-methoxy-2-naphthyl)-2-trimethylsiloxypropan-1-one is obtained. Regeneration of the hydroxyl group by hydrolysis affords (S) 2-hydroxy-1-(6-methoxy-2-naphthyl)propan-1-one. Further reaction with methanesulfonyl chloride then affords (S) 1-(6-methoxy-2-naphthyl)-2-methanesulfonyloxy propan-1-one, which is processed according to step A. Alternatively, the ketone can first be ketalized according to step A and the regeneration of the hydroxyl group and the formation of the sulfonate ester can occur subsequently but prior to step B.
Sources & evidence
- ORD record
- ord-e6295bd35c4246479ba9afe8ce42fcd3
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210258
Reaction notes
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