Aluminum(III) Chloride → HCID 67422783, compound

HRID 1393003Notes

Reaction equation

HRID 1393003 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH:7]3[C:14]4([CH2:15][CH2:16][C:5]=2[CH:4]=1)[CH:10]([CH2:11][N:12]([C:17](=[O:19])[CH3:18])[CH2:13]4)[CH2:9][CH2:8]3.[Cl-].[Al+3].[Cl-].[Cl-]>C(S)C>[OH:2][C:3]1[CH:21]=[CH:20][C:6]2[CH:7]3[C:14]4([CH2:15][CH2:16][C:5]=2[CH:4]=1)[CH:10]([CH2:11][N:12]([C:17](=[O:19])[CH3:18])[CH2:13]4)[CH2:9][CH2:8]3

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67423549HCID 67423549, compound

Product 1

HCID 67422783HCID 67422783, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Methoxy-5,6,6a,7,10,11-hexahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrol-8-yl)-ethanone (Example 5A) (55.0 mg, 0.19 mmol) was dissolved in ethanethiol (4 mL). Aluminum chloride powder (128 mg, 0.96 mmol) was added. The mixture was stirred at 0° C. for 1 h, quenched with NaHCO3 (satd.aq., 4 mL), and extracted with CH2Cl2 (5 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane, providing 46.2 mg (88.3%) of the title compound.

Workup

  1. customquenched with NaHCO3 (satd.aq., 4 mL)
  2. extractionextracted with CH2Cl2 (5 mL×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-d8dddaa7f4d5475991e07377ac56fad4
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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