2H-Pyran-4-acetic acid, tetrahydro-4-hydroxy-, ethyl ester synthesis
- Product Name:2H-Pyran-4-acetic acid, tetrahydro-4-hydroxy-, ethyl ester
- CAS Number:401811-99-2
- Molecular formula:C9H16O4
- Molecular Weight:188.22
Yield:401811-99-2 69%
Reaction Conditions:
with iodine;zinc in tetrahydrofuran; for 6 h;Heating / reflux;
Steps:
63
Reference Example 63; Ethyl (4-hydroxytetrahydro-2H-pyran-4-yl)acetate; To a solution of tetrahydro-4H-pyran-4-one (5.5 g, 51.6 mmol), a zinc powder (4.05 g, 61.9 mmol) and a small amount of iodine in tetrahydrofuran (60 ml) was added dropwise ethyl bromoacetate (6.28 ml, 56.7 mmol) under a nitrogen atmosphere. After heating under reflux for 6 hrs. , 10% sulfuric acid (50 ml) was carefully added under ice-cooling and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgS04 and concentrated under reduced pressure to give the title compound (6.73 g, 69%) as a colorless oil. 1H-NMR (CDC13) 8: 1 . 29 (3H, t, J=7.0 Hz) , 1. 62-1 . 68 (4H, m), 2.48 (2H, s), 3.67-4.00 (5H, m), 4.19 (2H, q, J=6.8 Hz).
References:
WO2005/105802,2005,A1 Location in patent:Page/Page column 128-129
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