Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | 3-(Benzyloxy)propanal | HCID 10888261 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22178189 | HCID 22178189 | — |
Reaction Steps
5.47 g (79.17 mmol) of isobutyric acid nitrile is added in drops at −65° C. to an LDA solution (produced from 33.64 g (79.17 mmol) of n-butyllithium 15% in hexane, (1.6 M) and 80.1 g (79.17 mmol) of diisopropylamine), and it is stirred for 20 minutes at −65° C. Then, a solution that consists of 10 g (60.9 mmol) of 3-benzyloxy-1-propanaldehyde in 20 ml of THF is added in drops (over 60 minutes). The temperature is kept at −65° C.! Then, it is stirred for one more hour. It is now heated to −20° C., a solution that consists of 20% sulfuric acid is added in drops, and the temperature is allowed to reach +10° C. Then, 50 ml of MTB-ether is added, and then the organic phase is separated. The organic phase is washed with water and then with saturated sodium bicarbonate. Finally, it is washed once more with water and then evaporated to the dry state in a vacuum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07358382B2 |
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| Source dataset | uspto-grants-2008_04 |
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| ORD ID | ord-4152116586a847fb931f43dee2d136ab |
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| Source note | uspto-grants-2008_04 |
|---|