2H-Pyran-4-carboxylicacid,tetrahydro-4-methyl-(9CI) synthesis
- Product Name:2H-Pyran-4-carboxylicacid,tetrahydro-4-methyl-(9CI)
- CAS Number:233276-38-5
- Molecular formula:C7H12O3
- Molecular Weight:144.17
443912-70-7
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233276-38-5
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Yield: 100%
Reaction Conditions:
with lithium hydroxide monohydrate;water in 1,4-dioxane;methanol at 20;
Steps:
B10 Example B10
Example B10
A solution of methyl 4-methyltetrahydro-2H-pyran-4-carboxylate (5.00 g, 31.6 mmol) in 1:1:1 dioxane/water/MeOH (60 mL) was treated with lithium hydroxide hydrate (5.31 g, 126 mmol) and stirred at RT overnight.
The mixture was partially concentrated, diluted with water and EtOAc and acidified to pH=1 with 6M HCl.
The layers were separated, the aqueous layer extracted with additional EtOAc (50 mL) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 4-methyltetrahydro-2H-pyran-4-carboxylic acid (4.61 g, 100%).
1H NMR (400 MHz, DMSO-d6): δ 12.29 (s, 1H), 3.65 (dt, J=11.8, 4.3 Hz, 2H), 3.33-3.32 (m, 2H), 1.87-1.86 (m, 2H), 1.35 (ddd, J=13.5, 9.9, 4.1 Hz, 2H), 1.13 (s, 3H).
References:
Deciphera Pharmaceuticals, LLC;Flynn, Daniel L.;Caldwell, Timothy Malcolm;Samarakoon, Thiwanka;Vogeti, Lakshminarayana;Kaufman, Michael D.;Patt, William C.;Ahn, YuMi US2014/275016, 2014, A1 Location in patent:Paragraph 0266
856255-87-3
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233276-38-5
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5337-03-1
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74-88-4
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871022-58-1
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233276-38-5
93 suppliers
$22.00/100mg
5337-03-1
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233276-38-5
93 suppliers
$22.00/100mg