2-Cyclohexen-1-one → HCID 58028210, compound

HRID 1261570Notes

Reaction equation

HRID 1261570 reaction equation
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH:10]=[CH:9]1>>[CH:1]1([C:8]2([OH:14])[CH2:13][CH2:12][CH2:11][CH:10]=[CH:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 178419650HCID 178419650, compound

Product 1

HCID 58028210HCID 58028210, compoundYield 93%

Procedure

According to Example 2, cyclopentylmagnesium bromide (1.00 M in THF, 2.10 mL; 2.10 mmol; 1.05 equiv) was reacted with cyclohexenone (192 mg; 2.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv). Gel filtration (silica; pentane:Et2O 9:1, 0.5 vol-% NEt3) afforded 1-Cyclopentyl-cyclohex-2-enol (7) as colorless oil (306 mg, 93%).

Workup

  1. filtrationGel filtration (silica; pentane:Et2O 9:1, 0.5 vol-% NEt3)

Sources & evidence

ORD record
ord-37e5e4cbbec9450e88f5f6a5de524c10
Source dataset
uspto-grants-2013_06
Patent number
US08470982B2

Reaction notes

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