Water → 8-Hydroxy-8-(5-thiazolyl)-1,4-dioxaspiro[4.5]decane

HRID 969584Notes

Reaction equation

HRID 969584 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.C([Li])CCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1.O>C1COCC1.CCOC(C)=O>[S:4]1[C:5]([C:21]2([OH:24])[CH2:22][CH2:23][C:18]3([O:25][CH2:15][CH2:16][O:17]3)[CH2:19][CH2:20]2)=[CH:6][N:7]=[CH:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 590174418-Hydroxy-8-(5-thiazolyl)-1,4-dioxaspiro[4.5]decaneYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-trimethylsilyl-thiazole (2.5 g, 15.89 mmol) in THF (20 mL) was added to a 1.6 M solution of n-butyllithium in hexanes (11.9 mL, 19.07 mmol) at −78° C. with stirring under N2. After being stirred at −78° C. for 0.5 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (2.48 g, 15.89 mmol) in THF (20 mL) was added to the solution via syringe and stirring was continued for 1 h at −78° C. Water (5 mL) and EtOAc were added, and the reaction mixture was warmed to room temperature and extracted with EtOAc three times. The combined organic layers were dried (MgSO4), filtered, and crystallized from EtOAc to yield 3.4 g (90%) of the desired product. MS (M+H)+=242.1.

Workup

  1. stirringAfter being stirred at −78° C. for 0.5 h
  2. stirringstirring
  3. extractionextracted with EtOAc three times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customcrystallized from EtOAc

Sources & evidence

ORD record
ord-404d792822c343bd98687f997ee79c13
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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