5-((Tert-butyldimethylsilyl)oxy)pentan-1-ol → HCID 59750708, compound

HRID 748686Notes

Reaction equation

HRID 748686 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Si:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Si:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:11]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[F:19])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 36143185-((Tert-butyldimethylsilyl)oxy)pentan-1-olHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 59750708HCID 59750708, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (30 ml) was dissolved the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (0.94 g, 3.1 mmol) obtained in Example 5, followed by the addition of 5-(t-butyldimethylsilyloxy)-1-pentanol (1.1 ml, 4.6 mmol) and cyanomethylenetri-n-butylphosphorane (1.0 g, 4.1 mmol). The resulting mixture was heated under reflux for 14 hours under an argon atmosphere. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=15:1), whereby the title compound (1.4 g, 87%) was obtained as a colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 14 hours under an argon atmosphere
  3. temperatureto cool down
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=15:1), whereby the title compound (1.4 g, 87%)
  7. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-570663c92872471f909bf96a132c1799
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…