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

HRID 1369217Notes

Reaction equation

HRID 1369217 reaction equation
[CH:1]([C:3]1[C:23]([O:24][CH3:25])=[CH:22][C:6]2[CH2:7][C:8]3[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=3[CH:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][C:5]=2[CH:4]=1)=O.Cl>[Pd].CC(O)=O>[CH3:25][O:24][C:23]1[C:3]([CH3:1])=[CH:4][C:5]2[CH2:11][CH:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][C:6]=2[CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53954755Ethyl (+/-)-10,11-dihydro-2-formyl-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 54360337Ethyl (+/-)-10,11-dihydro-3-methoxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-2-formyl-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate (220 mg, 0.65 mmol), 10% Pd/C (90 mg), glacial HOAc (15 mL), and conc HCl (2 mL) was shaken at RT under hydrogen (60 psi). After 20 hr, the mixture was filtered through celite®, and the filtrate was concentrated to afford the title compound (200 mg, 95%) as a colorless oil: MS (ES) m/e 325.2 (M+H)+.

Workup

  1. filtrationthe mixture was filtered through celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5dc424b85efe4398af43eb450ca8e41b
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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