Carbon Dioxide → HCID 66786970, compound

HRID 1016034Notes

Reaction equation

HRID 1016034 reaction equation
C([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.[C:22](=[O:24])=[O:23].Cl>C1COCC1.O>[OH:21][C:11]1([C:7]2[S:6][CH:10]=[C:9]([C:22]([OH:24])=[O:23])[N:8]=2)[CH2:12][CH2:13][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-olHCID 178418339Butyllithium

Product 1

HCID 66786970HCID 66786970, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (17.1 mL of 1.6 M solution in hexane, 27.35 mmol) was added to 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (3.00 g, 12.43 mmol) in THF (50 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, dry ice (10 g, 227 mmol) was added to the lithiated compound solution and stirred for 2 h at −78° C. Water was added and the solution was warmed to room temperature. The mixture was then treated with 1N HCl to pH 3 to 4 and extracted with EtOAc (3×). The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), and concentrated and chromatographed (EtOAc to 1% AcOH/EAOAc) to give 3.23 g of 2-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)-1,3-thiazole-4-carboxylic acid. MS (EI) calcd: (M+H)+=286.1; found: 286.0.

Workup

  1. stirringAfter being stirred at −78° C. for 1 h
  2. stirringstirred for 2 h at −78° C
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed (EtOAc to 1% AcOH/EAOAc)

Sources & evidence

ORD record
ord-f269b8b134d6486ab241d12377be8413
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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