(2,6-Dimethyl-4-triisopropylsilanyloxyphenyl)-(4-methoxymethoxyphenyl)methanol → HCID 66642691, compound

HRID 1170993Notes

Reaction equation

HRID 1170993 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:19])[C:3]=1[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=1)O>CCOC(C)=O.CC(O)=O.[Pd]>[CH3:19][C:4]1[CH:5]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])[CH:7]=[C:2]([CH3:1])[C:3]=1[CH2:20][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 66642856(2,6-Dimethyl-4-triisopropylsilanyloxyphenyl)-(4-methoxymethoxyphenyl)methanol

Product 1

HCID 66642691HCID 66642691, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

A degassed solution of crude (2,6-dimethyl-4-triisopropylsilanyloxyphenyl)-(4-methoxymethoxyphenyl)methanol (12.0 g, 26.84 mmol) and Pd/C (1.2 g) in EtOAc/HOAc (19/1) was stirred under an atmosphere of hydrogen (1 atm) at r.t. After 5 h, the catalyst was filtered through a pad of Celite, rinsed with ethyl acetate and the combined filtrates concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:9) to afford 4-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-methoxymethoxybenzene (4.0 g, 41.5% for two steps): 1H NMR (300 MHz, CDCl3): δ 6.93 (s, 4H), 6.63 (s, 2H), 5.16 (s, 2H), 3.94 (s, 2H), 3.50 (m, 3H), 1.58 (s, 6H), 1.29 (m, 3H), 1.13 (m, 18H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:19); Rf=0.80.

Workup

  1. filtrationthe catalyst was filtered through a pad of Celite
  2. washrinsed with ethyl acetate
  3. concentrationthe combined filtrates concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:9)

Sources & evidence

ORD record
ord-c55831fe86274a1c8a6babc8e1236260
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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