Tetrahydrofuran → 2,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazole

HRID 1585446Notes

Reaction equation

HRID 1585446 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[S:12]1[CH2:16][CH2:15][N:14]2[CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=[C:13]12>O>[OH:21][CH2:20][C:18]1[N:19]=[C:13]2[N:14]([CH:17]=1)[CH2:15][CH2:16][S:12]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18183084Ethyl 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 181830822,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazoleYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium aluminium hydride (280 mg, 7.3 mmol) was suspended in dry, redistilled THF (20 ml) under argon and treated dropwise with a solution (THF, 20 ml), of ethyl 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxylate (1.32 g, 6.7 mmol). After 2 h, water was added carefully until effervescence ceased when the mixture was filtered through Celite, the filter pad washed with THF and water and the filtrate and washings combined and evaporated to dryness under reduced pressure. The residue was evaporated twice from ethanol to give the title compound as a white solid (1.03 g, 100%); dH (250 MHz; CD3OD) 3.73-3.95 (2H, m), 4.06-4.30 (2H, m), 4.42 (2H, s), 7.04 (1H, s).

Workup

  1. customin dry
  2. distillationredistilled THF (20 ml) under argon
  3. filtrationwas filtered through Celite
  4. washthe filter pad washed with THF and water
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was evaporated twice from ethanol

Sources & evidence

ORD record
ord-a96755659a1149f1815962c7ca543e0b
Source dataset
uspto-grants-1999_08
Patent number
US05939066

Reaction notes

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