Acetic Acid → 3-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-one

HRID 1930702Notes

Reaction equation

HRID 1930702 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.N1([C:23](=[O:31])[CH2:24][CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][O:27]2)C=CN=C1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][C:23]([CH:13]1[C:14](=[O:17])[CH2:15][CH2:16][O:11][CH2:12]1)=[O:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 2733832Lithium HexamethyldisilazideHCID 593337451-(1H-imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one

Product 1

HCID 593337093-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-oneYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.283 ml, 6.83 mmol) was added to a stirred solution of tetrahydro-4H-pyran-4-one (0.601 ml, 6.51 mmol) in toluene (3 mL) at 0° C. and the resulting mixture was stirred for 2 minutes. 1-(1H-imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one (0.632 g, 3.25 mmol) toluene (1 mL) was added and the reaction mixture was stirred for 5 minutes before it was quenched with acetic acid (0.559 ml, 9.76 mmol) in water (4 mL). The organic layer was separated and purified by flash column chromatography (ethyl acetate in heptane, 0 to 40%) yielding 3-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-one (117 mg, 16%).

Workup

  1. stirringthe reaction mixture was stirred for 5 minutes before it
  2. customThe organic layer was separated
  3. custompurified by flash column chromatography (ethyl acetate in heptane, 0 to 40%)

Sources & evidence

ORD record
ord-ea8a6b88bc934c1293ed23aabbbdb6db
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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