Cyclobutanone → 4-(1-Hydroxycyclobutyl)benzonitrile

HRID 1260184Notes

Reaction equation

HRID 1260184 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[C:15]1(=[O:19])[CH2:18][CH2:17][CH2:16]1>C(OCC)C>[OH:19][C:15]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 764674-IodobenzonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 224816304-(1-Hydroxycyclobutyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Analogously to the process described in Example 5A/Step 1, 32.67 g (143 mmol) of 4-iodobenzonitrile, 75 ml (150 mmol) of 2 M isopropylmagnesium chloride solution in diethyl ether and 15.0 g (214 mmol) of cyclobutanone were used to obtain 13.31 g (78% of theory) of the title compound. The reaction time at RT in this case was 16 h, and, after the aqueous workup, the crude product was purified by means of suction filtration through 150 g of silica gel with 10:1→4:1 cyclohexane/ethyl acetate as the eluent.

Sources & evidence

ORD record
ord-52e34a9507a845f1b633a2b729c59e9f
Source dataset
uspto-grants-2013_06
Patent number
US08470811B2

Reaction notes

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