Dimethylformamide → 2-Methyl-4-(2-methyl-benzyloxy)-benzaldehyde

HRID 1993047Notes

Reaction equation

[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][C:7]1[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=1[CH2:9][O:10][C:11]1[CH:16]=CC(Br)=C[C:12]=1C.CN([CH:26]=[O:27])C>C1COCC1>[CH3:5][C:4]1[CH:16]=[C:11]([O:10][CH2:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[CH3:6])[CH:12]=[CH:2][C:3]=1[CH:26]=[O:27]

Participants

Conditions

Temperature: -78 °C

Procedure

A 2.5M solution of n-BuLi (2.1 mL, 5.26 mmol) in THF was added dropwise to a −78° C. solution of 31.2 (1.46 g, 5.01 mmol) in THF (25 mL). The reaction was stirred at −78° C. for 15 minutes and then DMF (3.3 mL) was added. Cooling was removed after 5 minutes and the reaction was allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and water and the aqueous layer was extracted 1 additional time with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated. The resulting residue was purified via radial chromatography (5% ethyl acetate in hexanes0 to yield 269 mg (22%) of 2-Methyl-4-(2-methyl-benzyloxy)-benzaldehyde (31.3). LC/MSD m/e: 241.2 (M+H).

Workup

temperatureCooling
customwas removed after 5 minutes
temperatureto warm to room temperature
customThe reaction was partitioned between ethyl acetate and water
extractionthe aqueous layer was extracted 1 additional time with ethyl acetate
dry with materialThe combined organic layers were dried (Na2SO4)
concentrationconcentrated
customThe resulting residue was purified via radial chromatography (5% ethyl acetate in hexanes0

Sources & evidence

ORD record: ord-ef8007be0cec414d9ce3e6d975620cdf
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649110B2

Reaction notes

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