Water → 8-(5-Methyl-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 969581Notes

Reaction equation

HRID 969581 reaction equation
[CH2:1]([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1([OH:21])[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH2:12]1.CI.O>C1COCC1.CCOC(C)=O>[CH3:1][C:10]1[S:6][C:7]([C:11]2([OH:21])[CH2:12][CH2:13][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:19][CH2:20]2)=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-olHCID 178418339Butyllithium

Product 1

HCID 590174448-(5-Methyl-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.6 M solution of n-butyllithium in hexanes (5.70 mL, 9.12 mmol) was added to 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (1.00 g, 4.14 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, methyl iodide (0.71 mL, 9.12 mmol) was added to the solution via syringe at −78° C. The reaction mixture was allowed to warm to room temperature slowly and stirred overnight. Water and EtOAc were added. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed using 20% EtOAc/hexanes to give 0.77 g (71%) of the title compound. MS (M+H)+=256.1.

Workup

  1. stirringAfter being stirred at −78° C. for 1 h
  2. stirringstirred overnight
  3. extractionThe aqueous layer was extracted with EtOAc three times
  4. washThe combined organic layers were washed with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customflash chromatographed

Sources & evidence

ORD record
ord-e75c290690114468955fb4ba1b37dbbf
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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