Sodium hydride → 3-[3-(tert-Butyl-dimethyl-silanyloxy)-propylsulfanyl]-propan-1-ol

HRID 2362301Notes

Reaction equation

HRID 2362301 reaction equation
[S:1]([CH2:6][CH2:7][CH2:8][OH:9])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C1COCC1>[C:15]([Si:12]([CH3:14])([CH3:13])[O:5][CH2:4][CH2:3][CH2:2][S:1][CH2:6][CH2:7][CH2:8][OH:9])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 663583,3'-Thiodipropan-1-ol

Product 1

HCID 866782203-[3-(tert-Butyl-dimethyl-silanyloxy)-propylsulfanyl]-propan-1-olYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3,3′-thiodipropanol (900 mg, 6 mmol) in THF (3 ml) was added dropwise to a suspension of sodium hydride (240 mg, 6 mmol) in THF (15 ml) under an atmosphere of N2. The reaction mixture was stirred at RT for 30 mins, then a solution of tert-butyldimethylsilylchloride (900 mg, 6 mmol) in THF (2 ml) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane to give the title compound as a colourless oil (793 mg).

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with 20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-18f887503eab4b639f7a474176e3818d
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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