Dichloromethane → HCID 178471767, compound

HRID 220140Notes

Reaction equation

HRID 220140 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.[Al+3].[Cl-].[Cl-].[Cl-].[C:26](Cl)(=[O:28])[CH3:27]>C(OCC)(=O)C>[C:26]([C:4]1[CH:5]=[CH:6][C:1]([C@H:7]2[CH2:8][CH2:9][C@H:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:12]2)=[CH:2][CH:3]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178471766HCID 178471766, compound

Product 1

HCID 178471767HCID 178471767, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round bottom flask with a stir bar was charged with the product of Example 1B (3 g, 12.2 mmol) and 60 mL of dichloromethane. The reaction solution was cooled to 0° C. and AlCl3 (4.86 g, 36.5 mmol) was added in portions. The mixture was allowed to stir for 20 min, and then acetyl chloride (954 μL, 13.4 mmol) was added dropwise. After stirring for 15 minutes, the reaction mixture was slowly pored into a beaker with ice water and diluted with 120 mL of ethyl acetate. The layers were separated and the organic layer washed with 1 N NaHCO3 (×2) brine (×2), dried over Na2SO4, and filtered. Evaporation of the solvents afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04-1.17 (m, 2 H), 1.18 (t, 3 H), 1.39-1.62 (m, 3 H), 1.68-1.88 (m, 5 H), 2.17-2.26 (m, 2 H), 2.52-2.57 (s, 3 H), 4.07 (q, J=7.12 Hz, 2 H), 7.25-7.46 (m, 2 H), 7.77-7.94 (m, 2 H) MS (ESI) m/z 247 [M+H]+.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customThe layers were separated
  3. washthe organic layer washed with 1 N NaHCO3 (×2) brine (×2)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customEvaporation of the solvents

Sources & evidence

ORD record
ord-a9f7a4742248467a8320fe3da1aff58f
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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