Chlorotrimethylsilane → 4-Methoxy-2,2,8,8-tetramethyl-6-methylidene-3,7-dioxa-2,8-disilanon-4-ene

HRID 326059Notes

Reaction equation

HRID 326059 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CN(C)CCN(C)C.[CH3:21][Si:22]([CH3:32])([CH3:31])[O:23][C:24]([CH3:30])=[CH:25][C:26]([O:28][CH3:29])=[O:27].[CH3:33][Si:34](Cl)([CH3:36])[CH3:35]>C1COCC1>[CH3:29][O:28][C:26]([O:27][Si:34]([CH3:36])([CH3:35])[CH3:33])=[CH:25][C:24]([O:23][Si:22]([CH3:31])([CH3:21])[CH3:32])=[CH2:30]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2733746Methyl 3-[(trimethylsilyl)oxy]-2-butenoateHCID 178418339Butyllithium

Product 1

HCID 534150304-Methoxy-2,2,8,8-tetramethyl-6-methylidene-3,7-dioxa-2,8-disilanon-4-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To diisopropylamine (6.8 ml, 48 mm) in THF at 0° C. is added 30 ml of 1.6 M n-butyllithium (48 mm), then 6.5 ml tetramethylethylenediamine (TMEDA, 48 mm) cooled to -78° C. Then 7.6 g (40 mm) of methyl 3-trimethylsilyloxybut-2-enoate is added over 5 minutes at -70° C. The mixture is stirred at -75° for 10 minutes, then 8 ml (48 mm) trimethylsilylchloride is added over 5 minutes at -75° C. The solution is warmed to room temperature and concentrated in vacuo. The residue is slurried in 500 ml of n-hexane, and solids filtered off. The filtrate is concentrated in vacuo, B.P.=75°-76° C. at 0.3 mm Hg.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationsolids filtered off
  3. concentrationThe filtrate is concentrated in vacuo, B.P.=75°-76° C. at 0.3 mm Hg

Sources & evidence

ORD record
ord-4172a8ee8ba14a93a9e083cc24e42725
Source dataset
uspto-grants-1984_04
Patent number
US04444685

Reaction notes

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