Methanol → HCID 67247139, compound

HRID 410465Notes

Reaction equation

HRID 410465 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][C@@H:7]1[CH3:13])=[O:5])[CH3:2].[S:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[Li]CCCC.CO>C1COCC1.O.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([OH:12])([C:15]2[S:14][CH:18]=[CH:17][N:16]=2)[CH2:8][CH:7]1[CH3:13])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 9256ThiazoleHCID 12561744HCID 12561744, compoundHCID 178418339Butyllithium

Product 1

HCID 67247139HCID 67247139, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (−78° C.) solution of cis-2-methyl-4-oxo-cyclohexanecarboxylic acid ethyl ester (22 g, 119 mmol) and thiazole (16.9 mL, 239 mmol) in THF (154 mL) was added nBuLi (1.6 M in Hex, 74.6 mL, 119 mmol) dropwise at such a rate that the internal temperature was maintained <−65° C. The reaction mixture was stirred for 30 min, MeOH (4.83 mL, 119 mmol) was introduced, and the reaction warmed to room temperature where it was diluted with water and EtOAc. The layers were separated, the organic layer dried with MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography to afford 4-hydroxy-2-methyl-4-thiazol-2-yl-cyclohexanecarboxylic acid ethyl ester (21 g, 78 mmol).

Workup

  1. temperaturewas maintained <−65° C
  2. customThe layers were separated
  3. dry with materialthe organic layer dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-51307a69a40d4b9aad7f5bdaa5faf95e
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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