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

HRID 2103360Notes

Reaction equation

HRID 2103360 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 72.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-butyllithium (5.70 mL of 1.6 M solution in hexane, 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 lithiated compound 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 (3×). The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed using 20% EtOAc/hexane to give 0.77 g of the title compound in 71% yield. MS (EI) (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 (3×)
  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-880a07ec13154a7f8202d65f0ad629e7
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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