tert-Butyl hydroperoxide → 1H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-, methyl ester

HRID 547987

반응식

HRID 547987 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2.C([O:20]O)(C)(C)C>C1(C)C=CC=CC=1.C(#N)C.CC(C)[O-].[Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([OH:20])([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2

참가 물질

6

반응물 2

HCID 6410tert-Butyl hydroperoxideHCID 110423911H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester3회

생성물 1

HCID 109775851H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-, methyl ester수율 89%

시약·촉매·용매 3

HCID 3083750Zirconium(4+) propan-2-olate촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
30 °C

실험 절차

To a solution of methyl 5-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate (also known as methyl 5-chloro-1-oxo-2,3-dihydroindene-2-carboxylate) (0.500 g, 2.23 mmol) (Formula IIa wherein R1 is OCH3 and R4 is Cl) and zirconium(1V) isopropoxide (0.0086 g, 0.022 mmol) in toluene (1.34 g, 1.56 mL) at 30° C. was added an aqueous solution of tert-butyl hydroperoxide (70%, 0.316 g, 2.46 mmol). The reaction mixture was stirred for 24 hours at 30° C. and then diluted with acetonitrile (about 6 mL). Quantitative HPLC analysis showed 92% conversion of methyl 5-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate, forming racemic methyl 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-1H-indene-2-carboxylate in 89% yield (97% chemoselectivity).

후처리

  1. customat 30° C.

출처 및 근거

ORD 기록
ord-4932bb66191d4e22ae50ef1098387465
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939685B2

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