Sodium Acetate → Methyl dihydrojasmonate, cis-(+)-

HRID 2373

Reaction equation

[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C@@H:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C([O-])(=O)C.[Na+]>>[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C@@H:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Reactant 3

HCID 517045Sodium Acetate

HCID 7075801methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

HCID 178418287HCID 178418287, compound

Product 1

HCID 1738122Methyl dihydrojasmonate, cis-(+)-Yield 94.9%

Procedure

This ester (2.85 g) was then oxidized by means of PCC, in the presence of sodium acetate, in a manner analogous to the method described in Example 1 d), to yield 2.68 g of the desired methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (colorless oil; purity 98.5%; yield 92.7%).

Workup

customdescribed in Example 1 d

Sources & evidence

ORD record: ord-5e5ea1bad7f34a958fa0ed6555062f7d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728866

Linked notes

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