Water → HCID 9949118, compound

HRID 392385Notes

Reaction equation

HRID 392385 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[K+].Br[CH2:26][C:27]#[N:28].O>O1CCCC1>[C:27]([CH2:26][CH:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:16])#[N:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 82127Potassium hydrideHCID 2560863,3-Diphenyl-2,3-dihydro-1H-inden-1-one2×

Product 1

HCID 9949118HCID 9949118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Spiro[3,3-diphenyl-2,3-dihydro(1H)indene-1,3′-2′-cyanooxirane] (Compound 5) and 2-cyanomethyl-3,3-diphenylindanone (Compound 9) were synthesized as follows: 3,3-diphenylindanone (Compound 2), 5.0 g (0.0176 mole) and 2.62 g (0.0229 mole) of potassium hydride were stirred at room temperature in 40 mL of tetrahydrofuran. After the gas evolution subsided (approx. 45 min), 1.5 mL (0.0215 mole) of bromoacetonitrile was added. The dark red mixture was stirred for 1 hour and then 50 mL of water was added. The mixture was extracted three times with 75 mL of ethyl acetate. The combined organic extracts were concentrated in vacuo, loaded onto a silica gel column and eluted with 10% ethyl acetate in hexane. Three fractions were collected. After evaporation of the solvent, the first fraction yielded unreacted starting material (3.5 g). The second fraction yielded 0.49 g (9% yield) of spiro[3,3-diphenyl-2,3-dihydro(1H)indene-1,3′-2′-cyanooxirane] (Compound 5) as a white solid. The third fraction yielded 1.05 g (18% yield) of 2-cyanomethyl-3,3-diphenylindanone (Compound 9) as a yellow oil.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted three times with 75 mL of ethyl acetate
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. washeluted with 10% ethyl acetate in hexane
  5. customThree fractions were collected
  6. customAfter evaporation of the solvent
  7. customthe first fraction yielded unreacted

Sources & evidence

ORD record
ord-c48c6dc6a381461fb31443c89351f72e
Source dataset
uspto-grants-2004_10
Patent number
US06800658B2

Reaction notes

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