5-Tert-butyl-2-methylfuran-3-carbaldehyde → (5-Tert-butyl-2-methyl-3-furyl)(cyclohexyl)methanol

Reaction equation

[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([CH:11]=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:13]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O1CCCC1>>[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([CH:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[OH:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 574379815-Tert-butyl-2-methylfuran-3-carbaldehyde

HCID 178420632HCID 178420632, compound

Product 1

HCID 68514163(5-Tert-butyl-2-methyl-3-furyl)(cyclohexyl)methanolYield 62%

Procedure

An operation similar to that in Example 3 (2) was performed using 5-tert-butyl-2-methyl-3-furaldehyde (2.5 g) and 1N cyclohexylmagnesium bromide-tetrahydrofuran solution (23 mL) to give the title compound (2.3 g, 62%) as an oil.

Sources & evidence

ORD record: ord-4dfba799bc9545f4b4c44ed9c763f791
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Reaction notes

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