Chloroacetyl chloride → HCID 6504217, compound

HRID 590981Notes

Reaction equation

HRID 590981 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6]1.[Cl:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[Cl:15][CH2:16][C:17]([C:13]1[CH:12]=[CH:11][C:10]2[O:5][CH2:6][CH2:7][CH2:8][C:9]=2[CH:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 136319ChromanHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6504217HCID 6504217, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (III) (1.9 g, 14.25 mmol) was added portion wise at 0° C. to a solution of 3,4-dihydro-2H-1-benzopyran (9a) (450 mg, 3.35 mmol) and 2-chloroacetyl chloride (270 μL, 3.4 mmol) in dichloromethane (10 mL). After 3 hours, the mixture was quenched by a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/cyclohexane 40/60) to afford the desired product (9b) as a white yellow oil (250 mg, 1.19 mmol, 35%).

Workup

  1. customthe mixture was quenched by a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane/cyclohexane 40/60)

Sources & evidence

ORD record
ord-0b7a2a9d4cbd424a905fe1322f39a9ba
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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