1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester → Hedione

HRID 1281653ノート

反応式

HRID 1281653 の反応式
[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]>C(Cl)Cl>[CH3:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:3]1[C:2](=[O:1])[CH2:6][CH2:5][CH:4]1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

参加物

3

反応物 1

HCID 906341-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

生成物 1

HCID 102861Hedione収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a glovebox, into a 10 ml glass vial were placed 15.0 mg (0.0250 mmole) of [((R,R)-Me-Duphos)Ru(H)(cyclooctatriene)]BF4, 5.62 ml of CH2Cl2 and 11.23 g (50.0 mmole) of methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate. The resulting yellow solution was placed in a 75 ml autoclave, purged with hydrogen and pressurized to 90 bar of hydrogen. After 6 hours, the solution was exposed to air and passed through a column of silica gel to separate the catalyst. This gave a 99% yield of the desired Hedione® product with the following ratios of isomers: cis/trans=98/2; (+)-cis/(−)-cis=82.3/17.7, 64.6% ee.

後処理

  1. custompurged with hydrogen
  2. customto separate the catalyst

出典と根拠

ORDレコード
ord-42bf22b42039424bb502597f1148d66b
出典データセット
uspto-grants-2002_09
特許番号
US06455460B1

反応ノート

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