Citric Acid → 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde

HRID 1881867Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[S:13][CH:12]=[N:11][CH:10]=1.CCCCCC.C([Li])CCC.CN(C)[CH:27]=[O:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[S:13][C:12]([CH:27]=[O:28])=[N:11][CH:10]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole (7.44 g) in tetrahydrofuran (100 mL) was slowly added a 1.6M n-butyllithium hexane solution (25.6 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 30 min and N,N-dimethylformamide (8.0 g) was added. The reaction mixture was warmed to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.91 g, yield 82%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 228 (MH+).

Workup

temperatureThe reaction mixture was warmed to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-ed79df1c845d47929a72a73993b97575
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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