2,2-DIMETHYL-TETRAHYDRO-PYRAN-4-CARBALDEHYDE synthesis
- Product Name:2,2-DIMETHYL-TETRAHYDRO-PYRAN-4-CARBALDEHYDE
- CAS Number:34941-21-4
- Molecular formula:C8H14O2
- Molecular Weight:142.2
50675-23-5
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34941-21-4
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Yield:34941-21-4 90%
Reaction Conditions:
with Dess-Martin periodane in dichloromethane at 0; for 1 h;
Steps:
1 Step 1. 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde
To a solution of (2,2-dimethyltetrahydro-2H-pyran-4-yl)methanol (8 g, 55.5 mmol) in 260 mL DCM cooled to 0°C via ice/water bath was added Dess-Martin Periodinane (29.4 g, 69.3 mmol) in portions over 3 minute and the resulting mixture was stirred for lh at 0°C. The mixture was quenched with solid calcium hydroxide (excess) and stirred vigorously for 45 minutes. The solids were filtered off and washed with DCM (2 x 100 mL). The organics were concentrated to dryness under reduced pressure and the aldehyde was used as is for the next reaction sequence (7.1 1 g, 90%). 'HNMR (CD3OD) δ: 9.56 (s, 1H); 4.16 (dd, J = 3.3 and 16.1 Hz, 1H); 3.80 - 3.62 (m, 2H); 2.76-2.66 (m, 1H); 1.90-1.85 (m, 1H); 1.72-1.64 (m, 1H); 1.62-1.52 (m, 1H); 1.24 (s, 3H); 1.22 (s, 3H).
References:
WO2015/13835,2015,A1 Location in patent:Page/Page column 56
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34941-21-4
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34941-21-4
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