You could try refluxing in NaOMe/MeOH. The presence of methanol would preserve the methyl ester, while transesterification would produce methyl acetate as a by-product.
You could try refluxing in NaOMe/MeOH. The presence of methanol would preserve the methyl ester, while transesterification would produce methyl acetate as a by-product.
If you use methanol as a solvent and add a suitable base, you should end up with the correct product, since any MeOH attacking the protecting group you want to keep will simply re-form the methyl ester, whereas the acetate will cleave to give the unprotected alcohol.
You could potentially also achieve this using sodium methoxide/methanol to speed the reaction up, but standard potassium carbonate/methanol is usually just fine.
If you use methanol as a solvent and add a suitable base, you should end up with the correct product, since any MeOH attacking the protecting group you want to keep will simply re-form the methyl ester, whereas the acetate will cleave to give the unprotected alcohol.
You could potentially also achieve this using sodium methoxide/methanol to speed the reaction up, but standard potassium carbonate/methanol is usually just fine.
this makes sense as it would reversibly add/leave. how does cleavage take place mechanistically? Is it attack of methanol at the carbonyl then leaving group is the "rest of the ester"More
You could try refluxing in NaOMe/MeOH. The presence of methanol would preserve the methyl ester, while transesterification would produce methyl acetate as a by-product.
You could try refluxing in NaOMe/MeOH. The presence of methanol would preserve the methyl ester, while transesterification would produce methyl acetate as a by-product.
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If you use methanol as a solvent and add a suitable base, you should end up with the correct product, since any MeOH attacking the protecting group you want to keep will simply re-form the methyl ester, whereas the acetate will cleave to give the unprotected alcohol.
You could potentially also achieve this using sodium methoxide/methanol to speed the reaction up, but standard potassium carbonate/methanol is usually just fine.
If you use methanol as a solvent and add a suitable base, you should end up with the correct product, since any MeOH attacking the protecting group you want to keep will simply re-form the methyl ester, whereas the acetate will cleave to give the unprotected alcohol.
You could potentially also achieve this using sodium methoxide/methanol to speed the reaction up, but standard potassium carbonate/methanol is usually just fine.
More
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