1-Indanone → HCID 11435017, compound

HRID 2199372Notes

Reaction equation

HRID 2199372 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]1(=[O:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.[C:21](C(OCC(F)(F)F)=O)(F)(F)F.[NH4+].[Cl-]>C1COCC1>[CH2:21]=[C:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]1=[O:20]

Participants

6

Reactant 4

HCID 67351-IndanoneHCID 25517Ammonium ChlorideHCID 678882,2,2-Trifluoroethyl trifluoroacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 11435017HCID 11435017, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of LiHMDS (0.65 mL, 0.6 M in THF) was added a solution of 1-indanone (26 mg, 0.19 mmol) in THF (1.0 mL). The reaction mixture was allowed to warm to room temperature over 20 min, and then CF3CO2CH2CF3 was added (55 μL, 0.41 mmol). After an additional 20 min at room temperature, saturated aqueous NH4Cl (5 mL) was added, and the resulting mixture was extracted with EtOAc (3×5 mL). The organics were dried over Na2SO4 and concentrated under reduced pressure. Without purification, the crude mixture was immediately subjected to general procedure B. SiO2 flash chromatography (25% EtOAc in hexanes) afforded the 2-methlyene-1-indanone as a yellow oil (28 mg) in 98% yield.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (3×5 mL)
  2. dry with materialThe organics were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customWithout purification

Sources & evidence

ORD record
ord-7cb5cab4434c4513a88e8801a7e8380e
Source dataset
uspto-grants-2016_06
Patent number
US09359277B2

Reaction notes

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