HCID 19773097, compound → HCID 131717174, compound

HRID 1534606Notes

Reaction equation

HRID 1534606 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:9]=1)=[O:7].C(O[Mg][CH2:31][SiH:32]([CH3:34])[CH3:33])(C)C.[Cl-]>O1CCCC1>[OH:7][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:9]=1)[CH:31]([SiH:32]([CH3:33])[CH3:34])[O:7][CH:6]([CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 19773097HCID 19773097, compoundHCID 178459950HCID 178459950, compound

Product 1

HCID 131717174HCID 131717174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(naphth-2-ylmethoxy)phenyl 2-thiazolyl ketone (4.84 g; Note f. above) in tetrahydrofuran (5 ml) was added dropwise to a solution of isopropoxydimethylsilylmethylmagnesium chloride [prepared as described in J. Org. Chem., 1983, 48, 2120 from chloromethylisopropoxydimethylsilane (4.2 g) and magnesium powder (0.6 g) in tetrahydrofuran (7 ml)]. The mixture was stirred at ambient temperature for 1 hour, washed with saturated aqueous solution of ammonium chloride and then with a saturated aqueous solution of sodium chloride. The organic layer was separated, dried (Na2SO4) and evaporated to give 2-[1-hydroxy-2-isopropoxydimethylsilyl-1-(3-(naphth-2-ylmethoxy)phenyl)ethyl]thiazole as an oil.

Workup

  1. washwashed with saturated aqueous solution of ammonium chloride
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-49d8215641a144e4a9aa85b7eb7a991b
Source dataset
uspto-grants-1992_02
Patent number
US05089513

Reaction notes

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