Dimethylformamide → 5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde

HRID 470962Notes

Reaction equation

C([Li])CCC.[C:6]([Si:10]([CH3:20])([CH3:19])[O:11][CH2:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([CH3:9])([CH3:8])[CH3:7].CN([CH:24]=[O:25])C>O1CCCC1>[Si:10]([O:11][CH2:12][CH2:13][C:14]1[S:15][C:16]([CH:24]=[O:25])=[CH:17][CH:18]=1)([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (2.5M in hexanes, 30 mL) was added dropwise to a solution of tert-butyldimethyl(2-(thiophen-2-yl)ethoxy)silane (example 4, step a) (16 g) in tetrahydrofuran (250 mL) at −78° C. The reaction mixture was allowed to warm to 0° C. and stirred for 1 h. The reaction was then cooled to −78° C. and DMF (34 mL) was added over 10 min. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed with water, dried over sodium sulphate, filtered and the solvent evaporated in vacuo. Purification was by silica gel chromatography, eluting with 93:7 isohexane:ethyl acetate to give the subtitled compound as a colourless oil. Yield 15.4 g.

Workup

temperatureThe reaction was then cooled to −78° C.
temperatureto warm to room temperature
stirringstirred for 18 h
customThe reaction mixture was partitioned between water and ethyl acetate
customThe organic layer was separated
washwashed with water
dry with materialdried over sodium sulphate
filtrationfiltered
customthe solvent evaporated in vacuo
customPurification
washeluting with 93:7 isohexane

Sources & evidence

ORD record: ord-e9088fcaba874e829e0156efafeada33
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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