Diethyl Ether → HCID 59018074, compound

HRID 2381570Notes

Reaction equation

HRID 2381570 reaction equation
[CH3:1][Si:2]([CH2:5][CH2:6][O:7][CH2:8]Cl)([CH3:4])[CH3:3].[OH:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.CCN(CC)CC.CCOCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][Si:2]([CH2:5][CH2:6][O:7][CH2:8][O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 130194-CyanophenolHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 59018074HCID 59018074, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.63 ml (9.23 mmol) of SEM-Cl in 10 ml of dry DCM were added 1.00 g (8.39 mmol) of 4-hydroxy benzonitrile, 103 mg (0.84 mmol) of DMAP and 2.34 ml (16.8 mmol) of Et3N, stirring at RT under N2. After stirring overnight, 10 ml of ether were added and the solids filtered off. The filtrate was evaporated and the product purified by flash chromatography (20% ethyl acetate in petrol), obtaining 945 mg (3.79 mmol, 48%) of a colourless oil.

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe solids filtered off
  3. customThe filtrate was evaporated
  4. customthe product purified by flash chromatography (20% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-d8d2d17288aa4e768ae196cf7768d429
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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