Aluminium lithium hydride → 4-(Tert-butyldimethylsilyloxy)-benzenemethanethiol

HRID 1794059Notes

Reaction equation

HRID 1794059 reaction equation
C(=O)([S:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][SH:3])=[CH:10][CH:9]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86759958ethanethioic acid, S-[4-(tert-butyldimethylsilyloxy)benzyl] ester

Product 1

HCID 222200084-(Tert-butyldimethylsilyloxy)-benzenemethanethiolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

to a stirred solution of ethanethioic acid, S-[4-(tert-butyldimethylsilyloxy)benzyl] ester (30.7 g, 104 mmol) in dry THF (300 mL) at 0° C. under an argon atmosphere was added lithium aluminium hydride (5.9 g, 156 mmol). The reaction was stirred for 3 h at 0° C. The mixture was quenched by careful addition of EtOAc then water. The pH was brought to 5 with an aqueous solution of 10% HCl and the resulting slurry was filtered. The filtrate was extracted with EtOAc (2×100 mL) and the combined organic layers were washed successively with Rochelle's salt, brine, dried (MgSO4), filtered and concentrated to give the product as a green oil (22.1 g, 84%).

Workup

  1. customThe mixture was quenched by careful addition of EtOAc
  2. filtrationthe resulting slurry was filtered
  3. extractionThe filtrate was extracted with EtOAc (2×100 mL)
  4. washthe combined organic layers were washed successively with Rochelle's salt, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-50d69a8e615e44e38a08c2c3be6c77ac
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…