Chlorotrimethylsilane → HCID 23282359, compound

HRID 369670Notes

Reaction equation

HRID 369670 reaction equation
[CH2:1]([C:3]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([CH2:24][CH3:25])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=O)[CH3:2].[CH2:26]([SH:29])[CH2:27][CH3:28].C[Si](Cl)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:24]([C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:17]=[C:3]([CH2:1][CH3:2])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([S:29][CH2:26][CH2:27][CH3:28])[S:29][CH2:26][CH2:27][CH3:28])[CH3:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7848Propyl mercaptanHCID 10340Sodium CarbonateHCID 54234953HCID 54234953, compound

Product 1

HCID 23282359HCID 23282359, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 0.39 g of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 0.16 g of 1-propanethiol and 10 ml of chloroform was slowly added dropwise 0.16 g of trimethylsilyl chloride with stirring at room temperature. After stirring at room temperature for 3 hours, the reaction mixture was poured into 5% aqueous sodium carbonate solution and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.20 g of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-di(propylthio)ethoxy)butyloxy)benzene (yield, 41%), nD26.4 1.5300.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionextracted twice with diethyl ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-da3b99b0bce74bfb98ba4fca9c75543d
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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