1-Indanone → HCID 12640829, compound

HRID 733437Notes

Reaction equation

HRID 733437 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Li+].C[CH:13]([N-:15]C(C)C)C.C(P(=O)(OCC)OCC)#N>C1COCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([C:13]#[N:15])=[CH:2]1

Participants

5

Reactant 3

HCID 67351-Indanone2×HCID 76257Diethyl cyanophosphonateHCID 2724682Lithium diisopropylamide

Product 1

HCID 12640829HCID 12640829, compoundYield 829.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 1-indanone (100 g, 0.756 mole) in 1 L of dry THF was cooled to −10° C. followed by the addition of 38.7 ml of 2M LDA (75.6 mmole). After 20 min of stirring at −10° C. diethyl cyanophosphonate (126.28 ml, 0.8323 moles) was added over 1 hour. The reaction was warmed to room temperature until no indanone was visible by TLC. The reaction was again cooled to −10° C. and borotrifluoride diethyl etherate (191 ml, 1.513 moles) was added dropwise. After warming to room temperature THF was evaporated and the resulting dark oil dissolved in EtOAc, washed with water and dried over MgSO4. Evaporation of the EtOAc and distillation of the resulting oil afforded 88.4908 g of 1H-indene-3-carbonitrile (83% yield).

Workup

  1. additionwas added over 1 hour
  2. additionwas added dropwise
  3. customwas evaporated
  4. dissolutionthe resulting dark oil dissolved in EtOAc
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the EtOAc and distillation of the resulting oil

Sources & evidence

ORD record
ord-26b9a195eeb7407cbfe09c695fde68c1
Source dataset
uspto-grants-2009_09
Patent number
US07589204B2

Reaction notes

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