Aluminum(III) Chloride → 4,5-Dihydro-3-benzothiepin-1(2H)-one

HRID 1027900Notes

Reaction equation

HRID 1027900 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([S:13][CH2:14][C:15](Cl)=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[C:15]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][S:13][CH2:14]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 12704492HCID 12704492, compound

Product 1

HCID 2601454,5-Dihydro-3-benzothiepin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of aluminum chloride (12.21 g, 92 mmol) in CH2Cl2 (200 mL) was treated dropwise with a solution of Example 107B (9.83 g, 45.8 mmol) in CH2Cl2 (100 mL) over 35 minutes, stirred at ambient temperature for 30 minutes, poured into a flask containing ice water (˜400 mL) and transferred to a separatory funnel using ˜50 mL CH2Cl2. The layers were separated and the aqueous was extracted with CH2Cl2 (100 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with 20:1, 10:1 and 5:1 hexane:EtOAc to provide the title compound. 1H NMR (CDCl3) δ 2.99 (t, J=6.4 Hz, 2H), 3.19 (t, J=6.4 Hz, 2H), 3.55 (s, 2H), 7.21-7.26 (m, 1H), 7.40 (dt, J=7.6, 1.4 Hz, 1H), 7.50 (dt, J=7.5, 1.4 Hz, 1H), 7.93 (dd, J=7.8, 1.4 Hz, 1H); MS (M+H)+ m/z 179 (20%), (M+NH4)+ m/z 196 (100%).

Workup

  1. additionpoured into a flask
  2. customtransferred to a separatory funnel
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with CH2Cl2 (100 mL)
  5. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel eluting with 20:1, 10:1 and 5:1 hexane

Sources & evidence

ORD record
ord-f3579f3fe81548dba15f859d1ca83c5b
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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