HCID 131725854, compound → HCID 131725853, compound

HRID 1791974Notes

Reaction equation

HRID 1791974 reaction equation
[CH:1]1([Li])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH2:7]([N:9]1[CH:13]=[CH:12][C:11]([SiH:15]([CH3:17])[CH3:16])(Cl)[B:10]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:8]>C1COCC1>[CH2:7]([N:9]1[CH:13]=[CH:12][CH:11]([Si:15]([CH:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)([CH3:17])[CH3:16])[B:10]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:8]

Participants

4

Reactant 2

HCID 131725854HCID 131725854, compoundHCID 178506819HCID 178506819, compound

Product 1

HCID 131725853HCID 131725853, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of cyclopentadienyl lithium (0.16 g, 2.27 mmol) in 10 mL of THF was added slowly to a solution of 1-ethyl-3-chlorodimethylsilyl-2,3-dihydro-2-phenyl-1H-1,2-azaborole (0.60 g, 2.27 mmol) in 10 mL of THF at −50° C. The reaction mixture wag slowly warmed to 25° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was extracted with pentane. Solvent was removed from the extracts leaving the desired product as a brown oil (0.58 g, 87 percent).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with pentane
  3. customSolvent was removed from the extracts

Sources & evidence

ORD record
ord-637bc45e13214786913531fb8612dc35
Source dataset
uspto-grants-2006_07
Patent number
US07074865B2

Reaction notes

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