Diethyl Ether → HCID 54462554, compound

HRID 1199263Notes

Reaction equation

HRID 1199263 reaction equation
[CH:1]1([N-]C(C)C)[CH2:6]CCC[CH2:2]1.[Li+].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1.C[Si](C)(C)Cl.[CH:22]1([CH2:28][CH:29](OC(=O)CC(C)C)C=C)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CC[O:41]CC>CO>[CH:22]1([CH2:28][CH:29]=[CH:16][CH2:12][CH:13]([CH:1]([CH3:6])[CH3:2])[C:14]([OH:41])=[O:15])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 10877271Lithium cyclohexylisopropylamideHCID 14261111HCID 14261111, compound

Product 1

HCID 54462554HCID 54462554, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution, prepared as described in (a), of 6 mmol of lithium cyclohexylisopropylamide in abs. THF there are added dropwise, at -78°, first 2.3 ml (18 mmol) of trimethylchlorosilane and then 1.2 g (5 mmol) of isovaleric acid 1-cyclohexyl-3-buten-2-yl ester. The solution is maintained at -78° for 1 hour, heated to room temperature over a period of 11/2 hours and stirred at that temperature for 1 hours. the reaction mixture is cooled to 0°, hydrolysed by adding 0.5 ml of methanol, diluted with ether, washed with 1N HCl and brine, dried over MgSO4 and concentrated by evaporation in a rotary evaporator. The residue is distilled as described in (a) and yields the same product.

Workup

  1. customTo a solution, prepared
  2. temperatureThe solution is maintained at -78° for 1 hour
  3. temperaturethe reaction mixture is cooled to 0°
  4. washwashed with 1N HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated by evaporation in a rotary evaporator
  7. distillationThe residue is distilled
  8. customyields the same product

Sources & evidence

ORD record
ord-7529e245dc1e4601b83d66ba0732561a
Source dataset
uspto-grants-1990_02
Patent number
US04898977

Reaction notes

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