Chlorotrimethylsilane → HCID 18630283, compound

HRID 376686Notes

Reaction equation

C[N:2]([CH2:4][CH2:5]N(C)C)C.[Li][CH:10]([CH2:12]C)[CH3:11].[CH2:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:4]([NH:2][C:29](=[O:28])[C:25]1[C:12]([Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:10][CH:11]=[CH:27][C:26]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:5]

Participants

Reactant 5

HCID 6397Chlorotrimethylsilane

HCID 8028Tetrahydrofuran

HCID 8037N,N,N',N'-Tetramethylethylenediamine

HCID 8078Cyclohexane

HCID 178418400CID 53628100

Product 1

HCID 18630283HCID 18630283, compoundYield 39%

Conditions

Temperature: -78 °C

Procedure

This amide (2.25 g, 10 mmol) and TMEDA (1.2 eq) in THF were mixed and cooled to -78° C. and a 1.3 M s-BuLi solution in cyclohexane (2.2 eq) was added dropwise. The resulting reaction mixture was stirred at -78° C. for 30 min and TMSCl (1.2 eq) was added dropwise. The reaction was stirred at -78° C. for 30 min and allowed to warm to -30° C. The reaction was worked up in the usual manner. The crude product was purified by flash chromatography and recrystallization from hexanes to afford the title compound as a white solid (1.15 g, 39%). m.p. 159°-160° C.

Workup

customThe resulting reaction mixture
stirringThe reaction was stirred at -78° C. for 30 min
temperatureto warm to -30° C
customThe crude product was purified by flash chromatography and recrystallization from hexanes

Sources & evidence

ORD record: ord-923937270de34c7f93154c3d42b529b8
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE036562

Reaction notes

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