HCID 22467285, compound → HCID 22467320, compound

HRID 1934557Notes

Reaction equation

HRID 1934557 reaction equation
[Si:1]([O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:29][C:23]=2[CH:22]=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si](OC1C2CCC=C(C(OC)=O)CC=2C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:14]([Si:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][CH:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:29][C:23]=2[CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 22467285HCID 22467285, compoundHCID 22467308HCID 22467308, compound

Product 1

HCID 22467320HCID 22467320, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a mixture of methyl 1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-7H-benzocycloheptene-6-carboxylate and methyl 1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-5H-benzocycloheptene-6-carboxylate (1.50 g) in EtOAc (60 ml) was added 10% Pd-C (wet) (300 mg). The mixture was stirred under hydrogen atmosphere at room temperature for 7 hours. After removal of Pd-C by filtration, the filtrate was evaporated to give methyl 1-(tert-butyldiphenyl-silyloxy)-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (1.51 g) as an oil.

Workup

  1. customAfter removal of Pd-C
  2. filtrationby filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fcbd7fd3796444339b986eef54087b1c
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

Loading…