Pyridine → HCID 85218918, compound

HRID 2101229Notes

Reaction equation

HRID 2101229 reaction equation
[O:1]([CH:19]([CH3:24])[CH2:20][CH2:21][CH2:22][OH:23])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[S:31](Cl)([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32]>C(Cl)Cl>[O:1]([CH:19]([CH3:24])[CH2:20][CH2:21][CH2:22][O:23][S:31]([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[Si:2]([C:15]([CH3:16])([CH3:17])[CH3:18])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 69050986HCID 69050986, compound

Product 1

HCID 85218918HCID 85218918, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(t-Butyldiphenylsiloxy)-pentanol (15 g, 0.04 mol) was dissolved in methylene chloride (100 mL) containing pyridine (7 g). Tosyl chloride (15.3 g, 0.08 mol) was added slowly and the mixture stirred overnight. The mixture was washed with saturated NaHCO3 (2×100 mL) and the aqueous then backwashed with methylene chloride (100 mL). The organic phases were combined and washed with 2M HCl (100 mL) and water. The solution was dried over Na2SO4, evaporated and purified by column chromatography (light petroleum:ethyl acetate, 3:1) to give the title compound as a thick oil (yield 85%). δC (CDCl3, 62.9 MHz): 19.2, 21.7, 21.8, 26.9, 28.6, 31.8, 63.5, 70.6, 127.7, 127.9, 129.6, 129.9, 133.2, 133.9, 135.6 and 144.7

Workup

  1. washThe mixture was washed with saturated NaHCO3 (2×100 mL)
  2. washwashed with 2M HCl (100 mL) and water
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated
  5. custompurified by column chromatography (light petroleum:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-6b1685e7afa144ce894e2537014974aa
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

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