Benzyl Chloride → HCID 14064717, compound

HRID 652365

Reaction equation

HRID 652365 reaction equation
C([N-]C(C)C)(C)C.[Li+].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:10]1.[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:24]1([CH2:23][CH:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][CH:10]=2)[C:19]([O:21][CH3:22])=[O:20])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 74706Methyl indole-3-acetate2×HCID 2724682Lithium diisopropylamide

Product 1

HCID 14064717HCID 14064717, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a 2-liter three necked round bottom flask equipped with an addition funnel was added, under nitrogen, 300 mL of dry tetrahydrofuran (THF) and 68.75 mL of lithium diisopropylamide (1.92M in cyclohexane/THF, 132 mmol). The mixture was cooled to -78° C., and a solution of indole-3-acetic acid, methyl ester (11.36 g, 60 mmol) in 300 mL of dry tetrahydrofuran was added dropwise. The mixture was then allowed to sit at -78° C. for 15 minutes, and then a solution of benzyl chloride (7.59 g, 60 mmol) in 300 mL of tetrahydrofuran was added dropwise. The reaction mixture must be stirred vigorously so that the precipitated dianion of indole-3-acetic acid, methyl ester reacts completely with the benzyl chloride. After 3 hours, TLC analysis indicated complete consumption of starting material, and 200 mL of aqueous saturated ammonium chloride was added. The aqueous layer was separated and washed with ether (2×100 mL). The combined ether extracts were added to the organic layer which was dried over magnesium sulfate, filtered and concentrated to 15.0 g (quantitative yield) of red-brown oil. This material was reduced to the corresponding tryptophol without further purification.

Workup

  1. additionwas added, under nitrogen
  2. waitAfter 3 hours
  3. customconsumption of starting material, and 200 mL of aqueous saturated ammonium chloride
  4. additionwas added
  5. customThe aqueous layer was separated
  6. washwashed with ether (2×100 mL)
  7. additionThe combined ether extracts were added to the organic layer which
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8f29c478503041fa963b771aa75ae488
Source dataset
uspto-grants-1987_06
Patent number
US04670462

Linked notes

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