Dichloromethane → HCID 21712698, compound

HRID 2289441Notes

Reaction equation

HRID 2289441 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:10]2[S:11][CH:12]=[CH:13][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:22][O:23]C(Cl)Cl>O.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:10]2[S:11][C:12]([CH:22]=[O:23])=[CH:13][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6344Dichloromethane3×HCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 21712803HCID 21712803, compound

Product 1

HCID 21712698HCID 21712698, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene (0.80 g) and dichloromethane (CH2Cl2) was dropwise added to a mixture of aluminum chloride (AlCl3) (1.01 g) and CH2Cl2 (5 ml) under ice-water cooling, and was stirred under the same conditions for 15 minutes. A mixture of 1,1-dichloromethyl methyl ether (0.52 ml) and CH2Cl2 (3 ml) was thereto added, and was stirred under the same conditions for 10 minutes. The reaction mixture was added into a mixture of CHCl3, ice, and water. The separated organic layer was washed with water, and brine, and dried over MgSO4. After evaporation of the filtrate, the resulting oil was purified by chromatography on silica gel (n-hexane-AcOEt as eluent) to give 6-ethoxycarbonyl-2-formyl-4,5,6,7-tetrahydrobenzo[b]thiophene (0.33 g).

Workup

  1. additionwas thereto added
  2. stirringwas stirred under the same conditions for 10 minutes
  3. washThe separated organic layer was washed with water, and brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the filtrate
  6. customthe resulting oil was purified by chromatography on silica gel (n-hexane-AcOEt as eluent)

Sources & evidence

ORD record
ord-eeb6b2d9d01646f999e233de28d8b633
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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