Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | 3-Methyloxetane-3-carbaldehyde | HCID 18962468 | — |
| Reactant | HCID 66970597 | HCID 66970597 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 89534506 | HCID 89534506 | 43% |
Reaction Steps
1.0 M Magnesium m-methoxybenzene bromide in tetrahydrofuran (25 ml, 25.0 mmol) was added dropwise to a solution of 3-methyloxetane-3-carbaldehyde (0.5 g, 5.0 mmol) in 8 ml of tetrahydrofuran cooled to −70° C. The reaction medium was stirred for 4 hours at −70° C. and then allowed to return to 0° C., hydrolyzed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, washed with a saturated sodium chloride solution and evaporated. The residue obtained was purified by chromatography on a cartridge of silica gel (eluted with heptane/ethyl acetate, gradient from 90/10 to 60/40). 0.45 g of product was obtained in the form of a thick colorless oil. Yield=43%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09090596B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-07e8d1e2d6f440dcbfea06ee57643bd0 |
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| Source note | uspto-grants-2015_07 |
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