Toluene → HCID 66938091, compound

HRID 1363834Notes

Reaction equation

HRID 1363834 reaction equation
[Si:1]([O:8][CH:9]([CH2:33][CH2:34][C@:35]1([CH3:48])[C@H:39]([CH:40]=C)[O:38][C@H:37]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:36]1)[CH2:10][C:11]([O:13][C@@H:14]([C@@H:29]([CH3:32])[CH:30]=C)/[C:15](/[CH3:28])=[CH:16]/[CH2:17][O:18]CC1C=CC(OC)=CC=1)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([C:53]1[CH:58]=[C:57]([CH3:59])[CH:56]=[C:55](C(C)(C)C)[C:54]=1[OH:64])(C)(C)C.[C:65]1(C)C=CC=CC=1>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:12])[O:13][C@H:14](/[C:15](/[CH3:28])=[CH:16]/[CH2:17][O:18][CH2:59][C:57]2[CH:58]=[CH:53][C:54]([O:64][CH3:65])=[CH:55][CH:56]=2)[C@@H:29]([CH3:32])[CH:30]=[CH:40][C@@H:39]2[O:38][C@H:37]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[O:36][C@:35]2([CH3:48])[CH2:34][CH2:33]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 66937909HCID 66937909, compound

Product 1

HCID 66938091HCID 66938091, compound

Reagents, catalysts & solvents 1

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalyst

Procedure

(1S,2E)-4-[(4-methoxybenzyl)oxy]-2-methyl-1-[(1S)-1-methylprop-2-en-1-yl]but-2-en-1-yl 3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(2S,4R,5S)-4-methyl-2-phenyl-5-vinyl-1,3-dioxolan-4-yl]pentanoate (1.10 g, 1.63 mmol) and 2,6-di-tert-butyl-4-methylphenol (35.9 mg, 0.16 mmol) were dissolved in anhydrous toluene under Ar atmosphere. The reaction solution was heated to reflux for one hour. An anhydrous toluene (330 ml) solution of the second generation Hoveyda-Grubbs catalyst; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium (102 mg, 0.16 mmol) was added to the reaction solution. After the reaction solution was heated to reflux for five hours, it was cooled to room temperature. The reaction solution was filtered with silica gel (Fuji Silysia, commercial name Chromatorex, NH, 200-350 mesh) and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=8:1) to obtain the title compound (486.1 mg) as a white solid. This was obtained as a colorless needle by recrystallization (hexane:ethyl acetate).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for one hour
  3. temperatureAfter the reaction solution was heated
  4. temperatureto reflux for five hours
  5. filtrationThe reaction solution was filtered with silica gel (Fuji Silysia, commercial name Chromatorex, NH, 200-350 mesh)
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-dbb14e8009ba4844a0f58e5d5473b44e
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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