tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]-3-cyclohexen-1-yl}phenoxy) dimethylsilane → tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}phenoxy)dimethyl silane

HRID 585663Notes

Reaction equation

HRID 585663 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][CH3:30])=[CH:23][C:22]=3[O:31][CH2:32][O:33][CH3:34])=[CH:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([Si:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][CH2:17][CH:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][CH3:30])=[CH:23][C:22]=3[O:31][CH2:32][O:33][CH3:34])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22337758tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]-3-cyclohexen-1-yl}phenoxy) dimethylsilane

Product 1

HCID 22337754tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}phenoxy)dimethyl silaneYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added tert-butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]-3-cyclohexen-1-yl}phenoxy)dimethylsilane (118 mg, 0.24 mmol) and ethanol (15 ml). To the stirred solution, palladium (catalytic amount, 10% on activated carbon) was added in one portion. The reaction vessel was then evacuated and placed under an atmosphere of hydrogen. This process was repeated for 10 cycles before leaving under a hydrogen atmosphere. The reaction mixture was stirred vigorously for 17 hr then filtered through celite, washing with ethyl acetate. The filtrate was concentrated in vacuo affording the title compound as a colourless oil (118 mg, 100%) and a mixture of diastereoisomers. δH(CDCl3) 0.15 (6H, s), 0.92 (9H, s), 1.51 (2H, m), 1.63 (2H, m), 1.81 (2H, m), 1.94 (2H, m), 2.43 and 2.90 (1H, m), 2.84 and 3.02 (1H, m), 3.38 and 3.39 (3H, s), 3.40 (2×1.5H, s), 5.04 and 5.06 (2H, s), 5.08 and 5.10 (2H, s), 6.56 and 6.61 (1H, m), 6.70 (3H, m), 7.03 (2H, m), 7.11 (1H, d).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. customThe reaction vessel was then evacuated
  3. custombefore leaving under a hydrogen atmosphere
  4. filtrationthen filtered through celite
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cec23cad659344d59bcfa881fdf5ef9a
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

Loading…