Methyl iodide → 33223-78-8

HRID 2421814Notes

Reaction equation

HRID 2421814 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:13]([N-]C(C)C)(C)C.[Li+].CI>C1COCC1>[CH3:13][C:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-HCID 2724682Lithium diisopropylamide

Product 1

HCID 5986053133223-78-8

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

A solution of indane-1-carboxylic acid (4.1 g, 25.3 mmol) in THF (30 ml) was added in portions to a solution of lithium diisopropylamide in THF (2M, 27.8 ml, 55.6 mmol) with stirring at −20° C. The solution was then stirred at 35° C. for 1 hour, then cooled again to −20° C. and a solution of methyl iodide (2.05 ml, 32.89 mmol) in THF (10 ml) was added. The light yellow solution was warmed at 35° C. for 4 hours before extracting between HCl (2M) and EtOAc to yield the crude product (4.5 g) as a brown oil. This mixture was chromatographed on HPLC with EtOAc/hexane to yield 1-methyl-1-indanecarboxylic acid (1 g) and recovered starting material (700 mg)

Workup

  1. stirringThe solution was then stirred at 35° C. for 1 hour
  2. temperaturecooled again to −20° C.
  3. temperatureThe light yellow solution was warmed at 35° C. for 4 hours
  4. extractionbefore extracting between HCl (2M) and EtOAc
  5. customto yield the crude product (4.5 g) as a brown oil
  6. customThis mixture was chromatographed on HPLC with EtOAc/hexane

Sources & evidence

ORD record
ord-ff80e4c8c0be40d8ba0ec224f4d659de
Source dataset
uspto-grants-2011_06
Patent number
US07960310B2

Reaction notes

Loading…