1-Indanone → HCID 19047540, compound

HRID 742449Notes

Reaction equation

HRID 742449 reaction equation
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.[C:12]1(=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.[Cl-].[NH4+]>CCCCCC.CCOCC.C1COCC1>[O:9]1[CH:10]=[CH:11][C:7]([C:12]2([OH:21])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[CH:8]1

Participants

8

Reactant 4

HCID 67351-IndanoneHCID 25517Ammonium ChlorideHCID 891643-BromofuranHCID 178418339Butyllithium

Product 1

HCID 19047540HCID 19047540, compoundYield 104%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2.7 mL (0.027 mol) of 10M n-butyllithium in hexane in 70 mL of ether cooled to -78° C. was added 4 g (0.027 mol) of 3-bromofuran and the mixture was stirred for 15 min. To the above cooled mixture was added 3.17 g (0.024 mol) of indanone in 10 mL of THF and the mixture was allowed to warm to room temperature, and then stirred for 20 min. To the mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×100 mL), and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 5 g of crude 1-(3-furyl)-indan-1-ol, as an orange oil, which was used directly in the next step.

Workup

  1. stirringstirred for 20 min
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33fc585ebb3c4d0fba59bd5c2a3f9fc5
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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