Methanol → HCID 10360552, compound
Reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18]/C=C(\C)/CCC(OC)=O)=[C:16]([O:28][CH3:29])[C:15]([CH3:30])=[C:14]2[C:10]=1[C:11](=[O:31])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.N1C=CC=CC=1.[CH3:41][OH:42]>>[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:41]=[O:42])=[C:16]([O:28][CH3:29])[C:15]([CH3:30])=[C:14]2[C:10]=1[C:11](=[O:31])[O:12][CH2:13]2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]Participants
Procedure
A solution of methyl (E) 6-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (11.0 g) in methanol 125 ml), dichloromethane (125 ml) and pyridine (2 ml) was cooled to -78° C. and a stream of ozonized oxygen was bubbled through. After 45 minutes a blue color developed indicating the presence of unreacted ozone. Dimethyl sulfide (5 ml) was added and the cooling bath was removed. After 16 hours the solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate and then water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 2:1 hexane:ethyl acetate, so as to produce 2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)acetaldehyde, mp. 88°-92° C. (ether).
Workup
- customa stream of ozonized oxygen was bubbled through
- additionDimethyl sulfide (5 ml) was added
- customthe cooling bath was removed
- washAfter 16 hours the solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate
- dry with materialwater, then dried
- customevaporated
- customThe residue was chromatographed on silica gel
- washeluting with 2:1 hexane
Sources & evidence
- ORD record
- ord-a5b9f6afb33b4b4a9fb32fe8a93a4737
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05493030
Reaction notes
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