HCID 86588960, compound → HCID 11299590, compound
Reaction equation
[CH:1]([O:3][C@@H:4]1[CH2:9][C@H:8]([CH3:10])[CH2:7][CH2:6][C@H:5]1[C:11](=[O:13])[CH3:12])=O.C([C@@H:19]1[CH2:24][CH2:23][C@@H:22](C)[CH2:21][C@H:20]1OCC1C=CC=CC=1)=CC(=C)C>>[C:11]([C@@H:5]1[CH2:6][CH2:7][C@@H:8]([CH3:10])[CH2:9][C@H:4]1[O:3][CH2:1][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:13])[CH3:12]Participants
Procedure
As shown in Table 2,9-decene acetate (12) reacted smoothly to provide the carboxylic acid 9-acetoxy nonanoic acid (12a) in 93% yield. The alcohol functionality within the molecule appeared to be tolerated well in the case of isopulegol (13) which provided a combined yield of 78% of which (1R,2R,5R)-2-acetyl-5-methyl cyclohexanol (13a) was 44% and 34% was (1R,2R,5R)-2-acetyl-5-methyl cyclohexanol formate (13b). However, in contrast, the benzyl-protected version of this alcohol (14) provided 80% of the desired ketone, (1R,2R,5R)-(2-acetyl-5-methyl cyclohexyl)benzyl ether (14a). 13b and 14a are novel products. Substituted stilbenes 15 and 16 were cleanly converted into the corresponding acid products 15a and 16a, respectively, without difficulty in 91% and 95% yields, respectively.
Sources & evidence
- ORD record
- ord-c4ceb584be8745e488b7ac9d371ff877
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06787671B2
Reaction notes
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