Dimethylformamide → (R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane

HRID 74980Notes

Reaction equation

HRID 74980 reaction equation
[CH3:1][C@@:2]1([OH:8])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.CN(C=O)C.N1C=NCC=1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.CCOCC>[C:19]([Si:23]([CH3:26])([CH3:25])[O:8][C@:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1)([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11094567(R)-1-methylcyclohex-2-enol2×HCID 127446564H-Imidazole

Product 1

HCID 68008146(R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)-1-methylcyclohex-2-enol, 50a, (1.00 g, 8.91 mmol) in 20 dry DMF at room temperature was added 4H-imidazole (1.82 g, 26.74 mmol), tert-butyldimethylchlorosilane (2.02 g, 13.33 mmol) and a catalytic amount of 4-dimethylaminopyridine (0.11 g, 0.89 mmol). The resulting mixture was stirred at room temperature overnight. It was then diluted with ether, washed consecutively with water, citric acid and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The colorless crude oil 1.98 g was used directly in the next step without further purification.

Workup

  1. washwashed consecutively with water, citric acid and water
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe colorless crude oil 1.98 g was used directly in the next step without further purification

Sources & evidence

ORD record
ord-d8e9a94d9dc5491ba892b5f4ccd25b07
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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