Water → 2-{2-[Hydroxy-(3,4,5trimethoxyphenyl)methyl]-4-methoxyphenyl}-4,4-dimethyl-2-oxazoline

HRID 1019404Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[CH:26]=[O:27].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[OH:27][CH:26]([C:25]1[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:23]([O:22][CH3:21])[CH:24]=1)[C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2-(4-methoxyphenyl)-4,4-dimethyl-2-oxazoline (11.0 g) in tetrahydrofuran (50 ml) is cooled to −50° C., and thereto is added dropwise a 1.6 M solution of n-butyl lithium in hexane (36.8 ml) over a period of 20 minutes. The mixture is stirred at 40° C. for 30 minutes, and thereto is added dropwise a solution of 3,4,5-trimethoxybenzaldehyde (10.5 g) in tetrahydrofuran (30 ml) at the same temperature over a period of 10 minutes. After reaction at −30T for one hour, to the mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2-{2-[hydroxy-(3,4,5trimethoxyphenyl)methyl]-4-methoxyphenyl}-4,4-dimethyl-2-oxazoline (16.2 g) as listed in Table 53.

Workup

customAfter reaction at −30T for one hour
customThe ethyl acetate layer is separated
washwashed
customdried
concentrationconcentrated under reduced pressure
customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record: ord-8776830b405149348953de2700dec8d0
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486155B1

Reaction notes

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