Hydrochloric Acid → HCID 25150125, compound

HRID 2108673Notes

Reaction equation

HRID 2108673 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[C:17]([CH:25]([CH3:27])[CH3:26])[CH:16]=2)=[C:9]([CH3:28])[CH:8]=1)(=O)=O.[CH3:31][OH:32].C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.Cl.CN([CH:73]=[O:74])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([CH3:28])[C:10]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[C:17]([CH:25]([CH3:27])[CH3:26])[CH:16]=1)[C:31]([O:74][CH3:73])=[O:32]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 25150689HCID 25150689, compound

Product 1

HCID 25150125HCID 25150125, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxy-benzyl)phenyl trifluoromethanesulfonate (1.36 g, 3.05 mmol) in DMF (15.3 mL) in a bomb apparatus was added MeOH (2.5 mL, 61.6 mmol), Pd(OAc)2 (68 mg, 0.3 mmol), bis-(diphenyphosphino)propane (138 mg, 0.3 mmol) and Et3N (0.85 mL, 6.1 mmol). 60 psi of CO was then infused and the reaction mixture was stirred at 90° C. for 16 h. The cooled bomb was vented and the reaction mixture was poured into cold 1N HCl, extracted with EtOAc twice, the combined EtOAc were washed with brine, dried over Na2SO4, filtrated and concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:9) to afford methyl 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxybenzyl)benzoate as a yellow oil (1.00 g, 92.3%): 1H NMR (300 MHz, DMSO-d6): δ 7.66 (s, 2H), 7.16 (m, 5H), 6.90 (m, 2H), 6.71 (m, 1H), 5.15 (s, 2H), 3.98 (s, 2H), 3.87 (s, 2H), 3.85 (s, 3H), 3.26 (s, 3H), 2.25 (s, 6H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (15:85); Rf=0.50.

Workup

  1. extractionextracted with EtOAc twice
  2. washthe combined EtOAc were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate-hexanes (1:9)

Sources & evidence

ORD record
ord-c1b13324cac34b50a0fa9ed217559a03
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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