Diethyl Ether → Methyl dihydrojasmonate, cis-(+)-

HRID 363801Notes

Reaction equation

HRID 363801 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H+].[B-](F)(F)(F)F.O(CC)CC>ClCCl>[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 28118Tetrafluoroboric acidHCID 906341-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

Product 1

HCID 1738122Methyl dihydrojasmonate, cis-(+)-Yield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The reaction was carried out analogously to that described in example 6, but using 100 g (446 mmole) of methyl 3-oxo-2-pentyl-1-cyclopentene-acetate, 427 mg (1.34 mmole) of [(COD)Ru(2-methylallyl)2 ], 410 mg (1.34 mmole) of (-)-Me-DuPHOS and 26.5 ml of HBF4.O(C2H5)2 in dichloromethane (0.1M, 2.68 mmole). This corresponds to a catalyst concentration of 0.3 mole %, relative to the substrate. 170 ml of dichloromethane were added, and the mixture was hydrogenated at a temperature of 7.5° C. and a pressure of 5×106Pa for 70 h to obtain methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate in 99% yield, cis/trans ratio=99.2/0.8 and (+)-cis/(-)-cis ratio=84/16.

Workup

  1. customwas hydrogenated at a temperature of 7.5° C.

Sources & evidence

ORD record
ord-ae1f7adc524c410caad5c16093287a06
Source dataset
uspto-grants-1999_02
Patent number
US05874600

Reaction notes

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