Cyclopentanol → HCID 19838069, compound

Reaction equation

[OH:1][CH:2]1[NH:6][C:5](=[O:7])[CH:4]=[CH:3]1.[CH:8]1(O)[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([O:1][CH:2]2[NH:6][C:5](=[O:7])[CH:4]=[CH:3]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 2

HCID 7298Cyclopentanol

HCID 353549(R)-Dihydromaleimide

Product 1

HCID 19838069HCID 19838069, compound

Conditions

Temperature: 60 °C

Procedure

A mixture of 4.5 g of 1,5-dihydro-5-hydroxy-2H-pyrrol-2-one, 100 cm3 of cyclopentanol and 2.25 g of Amberlite IR 120 H is maintained for 8 hours at 60° C. It is then allowed to cool, is filtered, and evaporated to dryness. The residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1). 3 g of the expected product is obtained, m.p.=77°-78° C. crystallized from cyclohexane. After recrystallizing from a mixture of isopropyl ether-n-hexane, 1--1, m.p.=81°-82° C.

Workup

temperatureto cool
filtrationis filtered
customevaporated to dryness
customThe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1)

Sources & evidence

ORD record: ord-4f261d3d0f1d435d9d465e96d36835f4
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885307

Reaction notes

Loading…