Methanesulfonic Acid → HCID 21521870, compound

HRID 918268Notes

Reaction equation

HRID 918268 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C@H:13]1[C@:17]([CH3:22])([CH2:18][C:19]([OH:21])=[O:20])[C@@H:16]([OH:23])[CH2:15][CH2:14]1)[CH2:7][CH2:6]2.[CH:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH2:25].CS(O)(=O)=O>C1COCC1>[CH2:27]([O:26][CH:24]([O:23][CH:16]1[CH2:15][CH2:14][CH:13]([CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[C:17]1([CH3:22])[CH2:18][C:19]([O:21][CH:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:25])=[O:20])[CH3:25])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8108Butyl vinyl etherHCID 68145100HCID 68145100, compound

Product 1

HCID 21521870HCID 21521870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Contacting (1S, 2S, 5S) -5-(1,2,3,4 -tetrahydro-6-methoxy-2-naphthyl)-2-hydroxy-1-methylcyclopentaneacetic acid with butyl vinyl ether in THF containing methanesulfonic acid affords the stereochemically corresponding α-butoxyethyl 2-(α-butoxyethoxy)-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-1 -methylcyclopentaneacetate, in which the ester linkage is cleaved and the carboxyl reduced to hydroxy by contacting with lithium tetrahydroaluminate (1-) in THF. From the resultant alcohol, on esterification with acid chloride or anhydride in pyridine, followed by cleavage of the ether linkage via hydrochloric acid in acetone, the corresponding mono ester of the invention wherein the ester grouping is on the ethanolic side chain eventuates. Contacting such a mono ester with acid chloride or anhydride affords a di-ester of the invention.

Sources & evidence

ORD record
ord-f54557fec1d9426bb4adfd54801cb191
Source dataset
uspto-grants-1976_07
Patent number
US03970686

Reaction notes

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