1-Piperidinecarboxaldehyde → 4-(Tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde

HRID 390398Notes

Reaction equation

Br[CH2:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:28])[CH:4]=1.C([Li])(CC)C.C(N1CCCCC1)=[O:35]>O1CCCC1>[Si:9]([O:8][CH2:7][C:6]1[CH:26]=[CH:27][C:3]([CH:2]=[O:35])=[CH:4][C:5]=1[CH3:28])([C:22]([CH3:25])([CH3:24])[CH3:23])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (4-bromomethyl-2-methyl-benzyloxy)-tert-butyl-diphenyl-silane (3 g, 6.83 mmol) in tetrahydrofuran is added sec-butyl lithium at −78° C. under nitrogen atmosphere. The reaction mixture is warmed to 0° C. and stirred for 30 min. The reaction mixture is cooled to −78° C., N-formyl piperidine (1.13 mL, 10.24 mmol) is added, and the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture is quenched with water at 0° C. and extracted with EtOAc (50 mL×3). The combined organic layer is washed with brine solution, dried over magnesium sulphate, and concentrated under vacuum to give the title compound (3 g, 46%). ESI/MS m/z 389.1 (M+H)+.

Workup

temperatureThe reaction mixture is cooled to −78° C.
stirringthe reaction mixture is stirred for 3 hours at room temperature
customThe reaction mixture is quenched with water at 0° C.
extractionextracted with EtOAc (50 mL×3)
washThe combined organic layer is washed with brine solution
dry with materialdried over magnesium sulphate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-68da8bdba48d4336b817575e6a84a4a8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383642B2

Reaction notes

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