Potassium Phosphate, Dibasic → 2-tert-Butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-benzenethiol

HRID 356502Notes

Reaction equation

HRID 356502 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([S:19]C#N)=[CH:11][C:10]=1[CH3:22])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].SC[C@H]([C@@H](CS)O)O.OP([O-])([O-])=O.[K+].[K+]>CCO>[C:15]([C:13]1[CH:14]=[C:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:22])=[CH:11][C:12]=1[SH:19])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 446094D-1,4-DithiothreitolHCID 18798714tert-Butyl-(5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)-dimethyl-silane

Product 1

HCID 187986992-tert-Butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-benzenethiol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.02 g (9.00 mmol) of tert-butyl-(5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)-dimethyl-silane (prepared in Example HHH), 2.3 g (12 mmol) of dithiothreitol, EtOH (20 mL), and 0.02M potassium dibasic phosphate buffer (10 mL) was heated to 50° C. overnight. The mixture was cooled to room temperature, diluted with hexanes and washed with H2O. The organic layer was then dried (Na2SO4) and the solvent removed in vacuo to yield the title compound. 1H NMR (CDCl3) δ 0.20 (s, 6 H), 1.00 (s, 9 H), 1.44 (s, 9 H), 2.10 (s, 3 H), 3.42 (s, 1 H), 6.80 (s, 1 H), 7.04 (s, 1 H).

Workup

  1. customwas heated to 50° C. overnight
  2. washwashed with H2O
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3af43cbe6ef14515b46d020d771b9a53
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

Loading…