Benzyl Bromide → HCID 66923500, compound

HRID 452553

Reaction equation

HRID 452553 reaction equation
[CH:1]1([C:10]([O:12][CH3:13])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:24]([C:1]1([C:10]([O:12][CH3:13])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 3839612Methyl 2,3-dihydro-1H-indene-1-carboxylate

Product 1

HCID 66923500HCID 66923500, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. tetrahydrofuran solution containing methyl indane-1-carboxylate (2.10 g, 11.9 mmol) from Step A, was added a 1M tetrahydrofuran solution of NaHMDS (23.8 mL, 23.8 mmol). The mixture was stirred at −78° C. for 30 minutes. Benzyl bromide (1.49 mL, 12.5 mmol) was added and the reaction was warmed to 0° C. and stirred for 90 minutes. The reaction was quenched with aqueous sodium bicarbonate and then extracted into EtOAc (3×50 mL) and the combined organic washings were dried over MgSO4 and evaporated. The resulting residue was purified by column chromatography (98/2 hexanes/EtOAc) to afford of methyl 1-benzylindane-1-carboxylate (2.5 g, 79%) as a partially pure oil that was taken to the next step.

Workup

  1. temperaturethe reaction was warmed to 0° C.
  2. stirringstirred for 90 minutes
  3. customThe reaction was quenched with aqueous sodium bicarbonate
  4. extractionextracted into EtOAc (3×50 mL)
  5. dry with materialthe combined organic washings were dried over MgSO4
  6. customevaporated
  7. customThe resulting residue was purified by column chromatography (98/2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-d46bf892aa40439e802b96a341235bcd
Source dataset
uspto-grants-2013_07
Patent number
US08492387B2

Linked notes

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