Water → HCID 69524698, compound

HRID 2116807Notes

Reaction equation

HRID 2116807 reaction equation
O[CH2:2][C:3]1[C:4](=O)[CH2:5][CH2:6][C:7]=1[CH3:8].[CH:10]1([Li])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.O.[CH3:21]CCCCC>O1CCCC1.C1(C)C=CC=CC=1>[CH:10]1([CH2:2][C:3]2[C:4]([CH3:21])=[CH:5][CH2:6][C:7]=2[CH3:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 157681462-(Hydroxymethyl)-3-methylcyclopent-2-en-1-oneHCID 178506815HCID 178506815, compound

Product 1

HCID 69524698HCID 69524698, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(hydroxymethyl)-3-methyl-2-cyclopenten-1-one (2.98 g, 14.3 mmol) prepared in Example 15 was dissolved in 2 mL of tetrahydrofuran. This solution was added to a solution prepared by stirring indenyllithium (4.36 g, 35.8 mmol) dissolved in 30 mL of tetrahydrofuran at −30° C. The solution was stirred at room temperature for 12 hours. After adding 40 mL of water, the solution was extracted twice with 40 mL of diethyl ether using a separatory funnel. After taking the organic layer, moisture was removed with magnesium sulfate, and the solvent was removed using a rotary evaporator. A pure target compound (2.29 g, yield: 72%) was obtained by column chromatography (hexane:toluene=10:1) using silica.

Workup

  1. additionThis solution was added to a solution
  2. customprepared
  3. extractionthe solution was extracted twice with 40 mL of diethyl ether using a separatory funnel
  4. customwas removed with magnesium sulfate
  5. customthe solvent was removed
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-49e72938a9d64f988583a1f2fcb9c329
Source dataset
uspto-grants-2008_10
Patent number
US07439378B2

Reaction notes

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