Acetic Acid → HCID 10057540, compound
Reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13](C)C=C[C:6]=1S([O-])(=O)=O)(=[O:3])[CH3:2].C(O)(=[O:18])C>>[OH:18][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:14]=[CH2:13]Participants
3
Procedure
Alternatively, the acetoxy-tosylate could be prepared by initial reaction of EpB with acetic acid under palladium(0) catalysis to afford 1-hydroxy-2-acetoxy-3-butene. Tosylation under normal conditions (p-TsCl, Et3N, CH2Cl2, 88%) afforded the desired product. However, the isomeric inconsistency of the monoacetate material (acetyl migration during distillative purification) and the inseparability of the positional isomers of two intermediates posed significant problems, since the unwanted isomers complicated the enzymatic hydrolysis. Therefore, the former (diol) preparation is preferred.
Sources & evidence
- ORD record
- ord-a79a20add54647e8987ed79403f1a7e8
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05126268
Reaction notes
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