Chlorotrimethylsilane → 31469-20-2

HRID 1663403Notes

Reaction equation

HRID 1663403 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH:13]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][CH2:14]1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1COCC1.CCCCCC>[C:13]1(=[C:17]([O:19][CH2:20][CH3:21])[O:18][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 84700Ethyl cyclobutanecarboxylateHCID 178418339Butyllithium

Product 1

HCID 6723291331469-20-2

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.6 M hexane solution of n-butyllithium (2.72 mL, 4.34 mmol) was added to a solution of diisopropylamine (440 mg, 4.34 mmol) in THF (6 mL) at −78° C. over 5 minutes. The resultant solution was warmed to 0° C. for 30 min and cooled to −78° C. A solution of ethyl cyclobutanecarboxylate (464 mg, 3.62 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at −78° C. for 30 min. Chlorotrimethylsilane (0.597 mL, 4.71 mmol) was added. The mixture was warmed to room temperature over 1 h, quenched with saturated NaHCO3 (5 mL), diluted with diethyl ether (200 mL), washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated to give (cyclobutylidene(ethoxy)methoxy)trimethylsilane, which was taken to next step without further purification.

Workup

  1. temperatureThe mixture was warmed to room temperature over 1 h
  2. customquenched with saturated NaHCO3 (5 mL)
  3. additiondiluted with diethyl ether (200 mL)
  4. washwashed with water (20 mL), brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d68c8351833d41c0859f69ebb0fbb679
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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