N-Formylmorpholine → 3-((2-(tert-Butyldimethylsilyloxy)ethoxy)methyl)benzaldehyde

HRID 1255283Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C([Mg]Cl)(C)C.C([Li])CCC.N1(C=O)CC[O:33][CH2:32]C1>C1COCC1>[Si:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:19]=[CH:18][CH:17]=1)[CH:32]=[O:33])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: -10 °C

Procedure

(2-(3-Bromobenzyloxy)ethoxy)(tert-butyl)dimethylsilane [Aromatic Intermediate 25, step b] (2.3 g) was dissolved in THF (15 mL) and the solution cooled to −10° C. Isopropylmagnesium chloride (2M in THF, 1.2 mL) was added, followed by butyllithium (2.1M in hexanes, 2.4 mL). The mixture was stirred for 10 min before being added to a solution of morpholine-4-carbaldehyde (1.4 mL) in THF (15 mL). The mixture was stirred for 1 hour, then poured onto ammonium chloride solution (30 mL) and extracted into ether (2×30 mL). The combined ether extracts were washed with water and dried over sodium sulphate. The solvent was evaporated in vacuo to give the titled compound as a colourless oil. Yield 1.8 g.

Workup

stirringThe mixture was stirred for 1 hour
additionpoured onto ammonium chloride solution (30 mL)
extractionextracted into ether (2×30 mL)
washThe combined ether extracts were washed with water
dry with materialdried over sodium sulphate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-8ccbe509b6ba40cc8dafed22be103d23
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455483B2

Reaction notes

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