Ethyl Acetate → t-Butyl [[6-[2-[(t-butyldiphenylsilyloxy) methyl]phenyl]-6-[(4-chlorophenyl)sulfonyl]hexyl]oxy]dimethylsilane

HRID 748819Notes

Reaction equation

HRID 748819 reaction equation
[C:1]([Si:5]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)(=[O:29])=[O:28])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[Si:37]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59]O)([C:50]([CH3:53])([CH3:52])[CH3:51])([C:44]1C=CC=CC=1)[C:38]1C=CC=CC=1.C(C=P(CCCC)(CCCC)CCCC)#N.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:50]([Si:37]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][O:18][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[S:27]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)(=[O:28])=[O:29])([CH3:38])[CH3:44])([CH3:52])([CH3:53])[CH3:51]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 4622928Cyanomethylenetributylphosphorane2×HCID 10925936HCID 10925936, compound2×HCID 59750856HCID 59750856, compound

Product 1

HCID 59750749t-Butyl [[6-[2-[(t-butyldiphenylsilyloxy) methyl]phenyl]-6-[(4-chlorophenyl)sulfonyl]hexyl]oxy]dimethylsilaneYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The t-butyl [[2-[[(4-chlorophenyl)sulfonyl]methyl]benzyl]oxy]diphenylsilane (1.00 g, 1.87 mmol) obtained in Example 280 and 5-(t-butyldiphenylsilyloxy)-1-pentanol (0.68 ml, 2.8 mmol) were dissolved in toluene (7 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (650 mg, 2.69 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, 5-(t-butyldiphenylsilyloxy)-1-pentanol (0.34 ml, 1.4 mmol) and cyanomethylenetri-n-butylphosphorane (300 mg, 1.24 mmol) were added. Under an argon atmosphere, the resulting mixture was heated under reflux for 10 hours. The reaction mixture was then allowed to cool down. The residue obtained by concentrating the mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=15:1 eluate was concentrated under reduced pressure, whereby the title compound (932 mg, 1.27 mmol, 68%) was obtained as a pale yellowish brown oil.

Workup

  1. temperatureUnder an argon atmosphere, the resulting mixture was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureto cool down
  4. temperatureUnder an argon atmosphere, the resulting mixture was heated
  5. temperatureunder reflux for 10 hours
  6. temperatureto cool down
  7. customThe residue obtained
  8. concentrationby concentrating the mixture under reduced pressure
  9. customthe fraction obtained from the hexane

Sources & evidence

ORD record
ord-64244c48c3054368818386b3a5759662
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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