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

HRID 570874Notes

Reaction equation

HRID 570874 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-4699b641e2a34dd0a16b59966956c02e
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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