Chloroacetyl chloride → HCID 86618191, compound

HRID 2108502Notes

Reaction equation

HRID 2108502 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C([Mg]Cl)C.[Cl:18][CH2:19][C:20](Cl)=[O:21].C1COCC1>C(OCC)C.C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:13][O:12][C:10]([C:7]1[CH:8]=[C:9]2[C:4]([C:3]([C:20](=[O:21])[CH2:19][Cl:18])=[CH:2][NH:1]2)=[CH:5][CH:6]=1)=[O:11]

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 639844Methyl indole-6-carboxylateHCID 178461633HCID 178461633, compound

Product 1

HCID 86618191HCID 86618191, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 14 g (80 mmol) methyl indole-6-carboxylate, 40 mL (84 mmol) ethylmagnesium chloride (2M) in diethyl ether, 240 mL (240 mmol) zinc chloride (1M) in diethyl ether, 9.5 g (84 mmol) chloroacetyl chloride in 680 mL DCM was stirred at room temperature for 19 h. THF was added and diethyl ether and DCM were removed by evaporation. The mixture was treated with NH4Cl aq. and ethyl acetate. The aqueous phase was extracted with THF/ethyl acetate and the combined organic layers were washed with NaCl aq., dried with Na2SO4 and evaporated. The residue was washed with ethyl acetate and dried under vacuum at 50° C. to yield 4 g (20%) of the title compound as light yellow solid. MS (m/e): 250.1 (M−H).

Workup

  1. customdiethyl ether and DCM were removed by evaporation
  2. additionThe mixture was treated with NH4Cl aq. and ethyl acetate
  3. extractionThe aqueous phase was extracted with THF/ethyl acetate
  4. washthe combined organic layers were washed with NaCl aq.
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. washThe residue was washed with ethyl acetate
  8. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-e377020442e344848195a1a6c815685c
Source dataset
uspto-grants-2009_04
Patent number
US07514433B2

Reaction notes

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