Cuminaldehyde → HCID 59709742, compound

HRID 2220816Notes

Reaction equation

[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:12][O:13][C:14](=[O:33])[CH:15]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])P(OC)(OC)=O.CN(C)C(N(C)C)=N>O1CCCC1>[CH2:26]([O:25][C:23]([NH:22]/[C:15](=[CH:8]\[C:7]1[CH:10]=[CH:11][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)/[C:14]([O:13][CH3:12])=[O:33])=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: -78 °C

Procedure

4-Isopropylbenzaldehyde (2.00 g, 13.50 mmol) and methyl{[(benzyloxy)carbonyl]amino}-(dimethoxyphosphoryl)acetate (3.58 g, 10.80 mmol, 0.8 equivalent) are dissolved in tetrahydrofuran (20 ml) and cooled to −78° C. At −78° C., N,N,N′,N′-tetramethylguanidine (27.92 g, 0.24 mol, 11.5 equivalents) is added dropwise and then stirred at −78° C. for 3 h and subsequently at room temperature 3 days. The mixture is then extracted by shaking with ethyl acetate (twice 100 ml) and water, and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration, the crude product is chromatographed (Biotage 40M, cyclohexane/ethyl acetate 5/1). 3.47 g (73% of theory) of the title compound are obtained.

Workup

extractionThe mixture is then extracted
stirringby shaking with ethyl acetate (twice 100 ml) and water
washthe combined organic phases are washed with saturated sodium chloride solution
dry with materialdried over sodium sulphate
concentrationAfter concentration
customthe crude product is chromatographed (Biotage 40M, cyclohexane/ethyl acetate 5/1)

Sources & evidence

ORD record: ord-edf964f2a3c34d9e989d08a49dbbfad2
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368424B2

Reaction notes

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