Oxalyl chloride → HCID 178471771, compound

HRID 220136Notes

Reaction equation

HRID 220136 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.[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)(=O)[C:24]([Cl:26])=[O:25].[Cl-].[Ca+2].[Cl-]>ClCCl.O>[Cl:26][C:24]([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:25]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 5284359Calcium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 178471766HCID 178471766, compound

Product 1

HCID 178471771HCID 178471771, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution containing the product of example 1B (2.46 g, 10.0 mmol) and AlCl3 (2.66 g, 20.0 mmol) in 30 mL of dichloromethane at 0° C. was added oxalyl chloride (5 mL, 2 M solution in dichloromethane, 10 mmol). The mixture was stirred at room temperature for 30 minutes. After this time the reaction mixture was poured into an ice-cold solution containing calcium chloride (3 g) in 100 mL of water. The reaction mixture was stirred for 2 h and was extracted with dichloromethane (2×100 mL). The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure, and the resulting oil was purified by flash chromatography (ethyl acetate/hexane, 1/8) to afford the title compound as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.15 (m, 2H), 1.19 (t, J=7.06 Hz, 3H), 1.47 (m, 2H), 1.57-1.85 (m, 5H), 2.22 (d, J=6.75 Hz, 2H), 2.47 (m, 1H), 4.07 (q, J=7.06 Hz, 2H), 7.35 (d, J=8.29 Hz, 2H), 7.85 (d, J=8.29 Hz, 2H).

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionwas extracted with dichloromethane (2×100 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe resulting oil was purified by flash chromatography (ethyl acetate/hexane, 1/8)

Sources & evidence

ORD record
ord-789ba3c229254a88895060614547445b
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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