Water → 8-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 969569Notes

Reaction equation

HRID 969569 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]1[O:21][C:14]2([CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]2)[O:13][CH2:12]1.O>C1COCC1>[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:17]1([OH:20])[CH2:18][CH2:19][C:14]2([O:21][CH2:11][CH2:12][O:13]2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 9256ThiazoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.6 M solution of n-butyllithium in hexanes (8.1 mL, 12.92 mmol) was added to a solution of thiazole (1.0 g, 11.75 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (1.84 g, 11.75 mmol) in THF (10 mL) was added to the solution via syringe and stirring was continued for 3 h at −78° C. Water (5 mL) was added, and the reaction mixture was warmed to room temperature and extracted using EtOAc three times. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and chromatographed to yield 2.53 g (89%) of the desired compound. MS (M+H)+=242.2.

Workup

  1. stirringAfter being stirred at −78° C. for 1 h
  2. stirringstirring
  3. extractionextracted
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed

Sources & evidence

ORD record
ord-a0ec7dd4e4dc459c9db7b0bac330ca8a
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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