Chlorotrimethylsilane → HCID 67119986, compound

HRID 1182033Notes

Reaction equation

HRID 1182033 reaction equation
COC1C=CC=C[C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1.C([BH3-])#N.[Na+].C[Si](Cl)(C)C>C(#N)C.ClCCl>[CH2:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:10]=1)[CH3:13]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 17964393HCID 17964393, compound

Product 1

HCID 67119986HCID 67119986, compoundYield 157%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

960 mg of 1-[4-(2-methoxyphenoxy)phenyl]ethanone 69 are dissolved in 20 ml of acetonitrile and cooled in an ice bath, and 1.05 g of sodium cyanoborohydride and 2.01 ml of trimethylsilyl chloride are added. After 1 h, the mixture is diluted with dichloromethane and filtered through Celite, and the organic phase is extracted with sodium chloride solution, dried over sodium sulfate and concentrated. The residue is purified by chromatography (heptane:ethyl acetate 7:1). 710 mg of the desired product are obtained. C15H16O2 (228.29) MS (ESI): 246.20 (M+NH4+).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered through Celite
  3. extractionthe organic phase is extracted with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (heptane:ethyl acetate 7:1)

Sources & evidence

ORD record
ord-64caa2b16d33419884312a1c430ac865
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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