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

HRID 964480Notes

Reaction equation

HRID 964480 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.CN(CCN(C)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].Cl[Si:34]([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[CH3:35][Si:34]([CH3:37])([CH3:36])[O:27][C:26]([O:28][CH3:29])=[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

Conditions

Temperature
0 °C

Procedure

To dry diisopropylamine (52 mL, 0.39 mol) in THF (400 mL) at 0° C. under nitrogen was added n-BuLi (146 mL, 2.5M in hexanes, 0.365 mol) followed by TMEDA (48.5 mL, 0.32 mol). The solution was stirred at 0° C. for 30 min then cooled to -78° C. Methyl 3-trimethylsiloxybut-2-enoate, 1, (57.6 g, 0.3 mol) was added to the solution. After stirring for 10 min, chlorotrimethylsilane (61 mL, 0.48 mol) was added. The mixture was allowed to warm up to 0° C. and was then concentrated to dryness on a rotary evaporator at 0° C. (the compound is heat sensitive). Hexanes (dried over molecular sieves; 1 L) were added. The insolubles were removed by filtration and washed with hexanes. The combined filtrate was concentrated to dryness on a rotary evaporator at 0° C. and dried overnight, under high vacuum, at room temperature, to afford 82 g of crude product, 2, which was used in the next step without further purification.

Workup

  1. temperaturethen cooled to -78° C
  2. stirringAfter stirring for 10 min
  3. temperatureto warm up to 0° C.
  4. concentrationwas then concentrated to dryness on a rotary evaporator at 0° C. (the compound
  5. temperatureis heat sensitive)
  6. additionHexanes (dried over molecular sieves; 1 L) were added
  7. customThe insolubles were removed by filtration
  8. washwashed with hexanes
  9. concentrationThe combined filtrate was concentrated to dryness on a rotary evaporator at 0° C.
  10. customdried overnight, under high vacuum, at room temperature

Sources & evidence

ORD record
ord-48a25639c8884026b34037a6ec2bf30d
Source dataset
uspto-grants-1998_06
Patent number
US05770180

Reaction notes

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