Ethyl sulfide → Ethyl (+/-)-10,11-dihydro-3-hydroxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 1369218Notes

Reaction equation

HRID 1369218 reaction equation
C(SCC)C.[Al+3].[Cl-].[Cl-].[Cl-].C[O:11][C:12]1[C:13]([CH3:33])=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1>C(Cl)Cl>[OH:11][C:12]1[C:13]([CH3:33])=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

5

Reactant 3

HCID 9609Ethyl sulfideHCID 6451240Aluminum(III) ChlorideHCID 54360337Ethyl (+/-)-10,11-dihydro-3-methoxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 20592632Ethyl (+/-)-10,11-dihydro-3-hydroxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To dry CH2Cl2 (30 mL) cooled in an ice bath was added diethylsulfide (0.38 mL, 3.3 mmol) followed by AlCl3 (438 mg, 3.3 mmol). To this solution was added dropwise a solution of ethyl (±)-10,11-dihydro-3-methoxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetate (200 mg, 0.6 mmole) in dry CH2Cl2 (6 mL), and the resulting mixture was stirred at RT for 2 hr. The reaction was quenched with 1.0 N HCl (10 mL), and the layers were separated. The organic layer was dried (MgSO4) and concentrated on the rotavap to give the title compound (100 mg, 56%) as a colorless oil: MS (ES) m/e 311.2 (M+H)+.

Workup

  1. customThe reaction was quenched with 1.0 N HCl (10 mL)
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated on the rotavap

Sources & evidence

ORD record
ord-ae38b49e41ea470e8116cbfaf9a3dfa1
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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